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Enantioselective Total Synthesis of (+)-Cassiol

Petrova, Krastina V. and Mohr, Justin T. and Stoltz, Brian M. (2009) Enantioselective Total Synthesis of (+)-Cassiol. Organic Letters, 11 (2). pp. 293-295. ISSN 1523-7060. PMCID PMC2707596. doi:10.1021/ol802410t. https://resolver.caltech.edu/CaltechAUTHORS:PETol09

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Abstract

An enantioselective total synthesis of (+)-cassiol is reported. The complex derived from Pd-2(pmdba)(3) and enantiopure t-BuPHOX ligand catalyzes enantioconvergent decarboxylative alkylation to generate the quaternary carbon stereocenter at an early stage. The overall synthetic strategy involves a convergent late-stage coupling of two fragments. The synthesis features a longest linear sequence of eight steps.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol802410tDOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2707596/PubMed CentralArticle
ORCID:
AuthorORCID
Mohr, Justin T.0000-0002-7005-3322
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2008 American Chemical Society. Received October 19, 2008. We thank Samantha R. Levine and Michael R. Krout (Caltech) for helpful discussions and experimental assistance. We thank the NIH-NIGMS (R01 GM080269-01), Caltech Amgen Scholars Program (undergraduate fellowship to K.V.P.), Eli Lilly (predoctoral fellowship to J.T.M.), Amgen, Bristol-Myers Squibb, Merck Research Laboratories, Abbott Laboratories, Boehringer-Ingelheim, and Caltech for financial support.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
AmgenUNSPECIFIED
Eli LillyUNSPECIFIED
AmgenUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:POTENT ANTIULCEROGENIC COMPOUND; CARBON QUATERNARY STEREOCENTERS; DECARBOXYLATIVE PROTONATION; ASYMMETRIC CATALYSIS; ENOL ETHERS; ALKYLATION; ACID; DIHYDROXYLATION; (-)-CASSIOSIDE; CONSTRUCTION
Issue or Number:2
PubMed Central ID:PMC2707596
DOI:10.1021/ol802410t
Record Number:CaltechAUTHORS:PETol09
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:PETol09
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:13319
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Apr 2009 22:44
Last Modified:08 Nov 2021 22:36

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