The Stoltz Group
Natural Product Synthesis and Synthetic Methodology
California Institute of Technology • Pasadena, California


• The group's publication titled "A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation" has been featured in Synfacts, 2009, 708. The article can be found here.
• The group's synthesis of (+)-Cassiol has been featured in Synfacts, 2009, 712. The article can be found here.
• The group's latest publication titled "An efficient synthesis of the carbocyclic core of zoanthenol" has been published in Tetrahedron and can be found here.
• Brian was recently awarded the Raymond and Beverly Sackler Prize in the Physical Sciences. Congratulations!
• The group's latest publication titled "Synthetic efforts toward cyathane diterpenoid natural products" has been published in Nat. Prod. Rep. and can be found here.
• The group's latest publication titled "Unexpected decarbonylation during an acid-mediated cyclization to access the carbocyclic core of zoanthenol" has been published in Tetrahedron Lett. and can be found here.
• The group's publication titled "Palladium-Catalyzed Enantioselective Oxidation of Chiral Secondary Alcohols: Access to Both Enantiomeric Series" has been featured in Synfacts, 2009, 121. The article can be found here on the Synfacts page.
• Take a look at the group's three latest publications in Org. Synth. Titled "Preparation of (S)-2-Allyl-2-methylcyclohexanone", "Preparation of (S)-tert-ButylPHOX", and "The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-AcetylPhenyl)Acetate." They can be found here.
• The group's publication concerning "A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation" has been featured in Chemistry World's Totally Synthetic column. Take a look here.
• The group's latest communication, "Progress toward the Synthesis of the Transtaganolide/Basiliolide Natural Products: An Ireland-Claisen Approach", has been published in Tetrahedron Lett. and can be found here.
• The group's latest paper, "Side Chain Chemistry Mediates Backbone Fragmentation in Hydrogen Deficient Peptide Radicals", has been published in J. Proteome Res. and can be found here.
• Take a look at the group's two latest papers! The "Catalytic Enantioselective Approach to the Eudesmane Sesquiterpenoids: Total Synthesis of (+)-Carissone" and the "Enantioselective Total Synthesis of (+)-Cassiol" have both been published in Org. Lett. and can be found here.
• Pictures from the group holiday party are now online, and can be found here.
• The latest publication from the group describing "A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation" has been accepted to J. Am. Chem. Soc. and can be found here.
• The group's recent publication concerning "Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers" has been featured in the November issue of Synfacts.
• The group's latest paper, titled "Structural Features and Reactivity of (Sparteine)PdCl2: A Model for Selectivity in the Oxidative Kinetic Resolution of Secondary Alcohols", has been published in J. Am. Chem. Soc. and can be found here.
• Congratulations to Brian on receiving the 2008 Elias J. Corey Award For Outstanding Original Contribution in Organic Synthesis by a Young Investigator!
• The group's latest publication, "Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of Alkaloids", has been published in J. Am. Chem. Soc., and can be found here.
• The group's most recent review, "Natural products as inspiration for the development of asymmetric catalysis", has been published in Nature. Take a look here.
• The group's previous review concerning "Enantioselective Tsuji Allylations" has been listed among the most-accessed papers for Chem. Asian J. Take a look here.
• The group's most recent communication on "Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers" has been published in Angew. Chem. Int. Ed. You can find it here.
• The group's latest communication concerning "Palladium-Catalyzed Enantioselective Oxidation of Chiral Secondary Alcohols: Access to Both Enantiomeric Series" has been accepted and published in Angew. Chem. Int. Ed. Take a look here.
• The group's latest letter published in Nature has been featured in Chemical & Engineering News. Take a look at the article here.
• Several of the group's recent publications have been listed among the most accessed articles for the January - March 2008 period. "Homogeneous Pd-Catalyzed Enantioselective Decarboxylative Protonation" was listed among Org. Lett. communications. The most accessed list for J. Am. Chem. Soc. features both "The Catalytic Asymmetric Total Synthesis of Elatol" and "Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation".
• The group's latest publication "The Total Synthesis of (-)-Cyanthiwigin F by means of Double Catalytic Enantioselective Alkylation" has been accepted and published in Nature. Take a look here. Also, this article was recently the topic of a Chemistry World news article, as well as the subject of a Nature Chemistry research highlight.
• The group's publication concerning "The Catalytic Asymmetric Total Synthesis of Elatol" has been featured in the first issue of JACSβ! Take a look here.
• The group's previous publication concerning "Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (-)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (-)-Cephalotaxine, and (+)-Cephalotaxine" has been been featured on the Organic Chemistry Portal in Prof. Taber's highlight column titled "Advenures in Alkaloid Synthesis: (+)-α-Kainic Acid (Jung), 223AB (Ma), Pumiliotoxin 251F (Jamison), Spirotryprostatin B (Trost), (-)-Drupacine (Stoltz)". Take a look here.
• Take a look at a recent Science news article concering the King Abdullah University of Science and Technology (KAUST)!
• The group's previous publication concerning "Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (-)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (-)-Cephalotaxine, and (+)-Cephalotaxine" has been recognized as one of the Most-Accessed Articles in J. Org. Chem. for the year 2007! Take a look here.
• Professor Yujiro Hayashi recently visited Caltech to speak with the community. Take a look at some pictures of his visit here.
• Congratulations to Brian for being named one of twelve KAUST Global Research Partnership Investigators.
• Take a look at the group's latest publications! A paper concerning "Homogeneous Pd-Catalyzed Enantioselective Decarboxylative Protonation" has been published in Org. Lett., and a review concerning "The Biology and Chemistry of the Zoanthamine Alkaloids" has been accepted to Angew. Chem. Int. Ed. recently. Both can be viewed here.
• Congratulations to Eric Ferreira, who has just accepted a position as Assistant Professor at Colorado State University!
• Photos from the eighth annual Stoltz Bowl and Super Bowl party are available to view here.
• The group's latest paper, entitled "C-H Bond Functionalizations with Palladium(II): Intramolecular Oxidative Annulations of Arenes", has been published in Tetrahedron and can be viewed here.
• The group's latest communication concerning "Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation" has been published in J. Am. Chem. Soc., and can be found here.
• The group's latest paper on "The Catalytic Asymmetric Total Synthesis of Elatol" has been published in J. Am. Chem. Soc., and can be found here.
• Pictures from the group's holiday party are online, and can be viewed here.
• "Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (-)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (-)-Cephalotaxine, and (+)-Cephalotaxine" has been listed among the most accessed papers in J. Org. Chem. Take a look here.
• The group's latest paper concerning "Progress toward the Synthesis of the Basiliolides and Transtaganolides" has been published in Org. Lett., and can be found here.
• "Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis" has been listed among the most accessed papers in Org. Biomol. Chem.! Take a look here.
• Pictures from Brian's birthday party are online, and can now be viewed here.
• The group's latest review titled, "Enantioselective Tsuji Allylations" has been published in Chem. Asian J., and can be viewed here.
• The group's latest paper titled, "Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis", has been published in Org. Biomol. Chem. and the publication can be found here.
• The group's latest publication on "Preparation of 3,3-disubstituted oxindoles by addition of malonates to 3-halo-oxindoles" has been published in Tetrahedron Letters, and can be viewed here.
• J. Am. Chem. Soc. has published "The Inner-Sphere Process in the Enantioselective Tsuji Allylation Reaction with (S)-t-Bu-phosphinooxazoline Ligands", a paper which represents the collaborative efforts of the Stoltz group and the Goddard group. The publication can be found here.
• Photos from the Intermural Softball Playoffs are now available to view. Take a look here.
• The group's latest publication concerning "Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (-)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (-)-Cephalotaxine, and (+)-Cephalotaxine" has been accepted to J. Org. Chem. It is available to view here.
• The group's latest paper concerning "A Facile and Modular Synthesis of Phosphinooxazoline Ligands" has been published in Org. Lett., and is now available to view here.
• Photos from the second annual Stoltz group softball game are now online, and are available to view here.
• Congratulations to Stoltz group alumnus Doug Behenna, who recently received the 2007 McCoy Award for his doctoral thesis!
• Photos of the Second Annual Caltech Hamburger Eating Contest are available to view here. Our own Chris Gilmore and Amanda Jones ranked in with eleven and ten hamburgers, respectively. Congratulations to Amanda, who won the woman's competition this year!
• Take a look at the group's latest paper concerning the "Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization" in Angew. Chem. Int. Ed. here.
• Neil Garg (Stoltz Group Ph.D) accepted a faculty position at UCLA. Congratulations Neil!
• Andy Harned (Stoltz Group Postdoc) accepted a faculty position at the University of Minnesota. Congratulations Andy!
• Brian was recently promoted to Professor of Chemistry. Congratulations Brian!
• Photos of Stoltz Bowl VII are now available to view. Take a look here.
• The group's latest paper, "Synthesis of 2-Quinuclidonium by Eliminating Water: Experimental Quantification of the High Basicity of Extremely Twisted Amides" is now available in J. Am. Chem. Soc. to view online. Take a look here.
• Congratulations to Brian on his recent election as a 2006 American Association for the Advancement of Science Fellow, in recognition of his contributions to the field of chemistry!
• The group's latest paper concerning an "Oxidative Kinetic Resolution-Claisen Rearrangement Sequence to Enantioenriched Arylcycloalkenes" has been published in Synlett. Take a look here.
• The synthesis of 2-quinuclidonium tetrafluoroborate has been featured in C & E News as a Chemistry Highlight of 2006.
• The group's publication on "Catalytic Enantioselective Decarboxylative Protonation" has been featured on the chemistry webportal, organic-chemistry.org, which can be accessed here.
• Pictures of the group holiday party are now available to view. Take a look here.
• The group's latest article concerning "The development and scope of a versatile tandem Stille-oxa-electrocyclization reaction" has been published in Tetrahedron Lett. and is available to view online. Take a look here.
• Pictures of Brian's (belated) surprise birthday party for 2006 can be found here.
• "A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C-H and C-C Bond Insertion Reactions" has been listed as one of the ten most accessed communications for J. Am. Chem. Soc. for the July-September 2006 period. Take a look here.
• Congratulations to Doug Behenna on the successful defense of his thesis. Doug will be traveling to Harvard University to undertake a postdoctoral study in the group of E. J. Corey. Pictures of the defense party can be found here.
• Take a look at the group's latest paper concerning "The synthesis of C-3β functionalized indoles via a hydroboration/Suzuki–Miyaura coupling sequence" here.
• The group's latest publication on "The Utility of the Classical and Oxidative Heck Reactions in Natural Product Synthesis: Studies Directed toward the Total Synthesis of Dragmacidin F" has been published in Synlett. Take a look here.
• "Oxidative Cyclizations in a Nonpolar Solvent Using Molecular Oxygen and Studies on the Stereochemistry of Oxypalladation" has been listed among 100 current 'Hot Papers' for National Chemistry Week 2006. Take a look here.
• The group's latest publication, "Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin", has been published in J. Org. Chem. Check it out here.
• A recent Angew. Chem. Int. Ed. article concerning the history of 2-quinuclidone discusses the group's synthesis of 2-quinuclidonium tetrafluoroborate. Take a look at the article here, or the original publication here.
• Much of the group's asymmetric alkylation methodology has been featured in a recent Angew. Chem. Int. Ed. review article written by Shu-Li You and Li-Xin Dai. Take a look here.
• "The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone" has been listed among the most accessed communications in J. Am. Chem. Soc.! Take a look here.
• Take a look at the group's latest paper concerning "A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C-H and C-C Bond Insertion Reactions" in J. Am. Chem. Soc. here.
• Our group's newest paper on "Catalytic Enantioselective Decarboxylative Protonation" has been published in J. Am. Chem. Soc. You can take a look here.
• The group's latest paper on "A unified synthetic approach to the pyrazinone dragmacidins" has been published as a Feature Article in Chem. Commun. Take a look here.
• Pictures from the first annual softball game party have been added.
• "The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone" was featured as a "Research Highlight" in Nature! Take a look here.
• The group's newest paper on "Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate" has been published in Nature! It can be found here. Also, take a look at the forward to the article, written by Harry Wasserman, and the " Abstractions" section featuring Brian. This paper was also featured in C & E News.
Click here for archived news.
Chemistry 5a - Advanced Techniques of Synthesis and Analysis (Spring 2003)
Chemistry 41c - Organic Chemistry (Spring 2008)
Chemistry 242a - Chemical Synthesis (Fall 2007)
Chemistry 250 - Advances in Pharmaceutical Research (Spring 2003)

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