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Progress toward the Synthesis of Garsubellin A and Related Phloroglucins: The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core

Spessard, Sarah J. and Stoltz, Brian M. (2002) Progress toward the Synthesis of Garsubellin A and Related Phloroglucins: The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core. Organic Letters, 4 (11). pp. 1943-1946. ISSN 1523-7060. doi:10.1021/ol025968+. https://resolver.caltech.edu/CaltechAUTHORS:20170215-135249615

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Abstract

A highly diastereoselective single-step cyclization reaction provides access to the bicyclo[3.3.1]nonane core of the polyprenylated phloroglucin natural product garsubellin A. Further elaboration to a more functionalized analogue involves a sequential Claisen rearrangement/Grubbs olefin cross-metathesis strategy. Additionally, this strategy was extended to the preparation of the bis-quaternary carbon array found at the bridgehead positions of the phloroglucin natural products.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol025968+DOIArticle
http://pubs.acs.org/doi/suppl/10.1021/ol025968%2BPublisherSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2002 American Chemical Society. Received April 3, 2002. Publication Date (Web): May 4, 2002. The authors are grateful to the California Institute of Technology, the Camille and Henry Dreyfus Foundation (New Faculty Award to B.M.S.), Merck Research Laboratories, and Pharmacia (graduate fellowship to S.J.S.) for generous financial support. The Grubbs, MacMillan, and Hsieh-Wilson labs are acknowledged for helpful discussions and the use of chemicals and instrumentation. We thank Larry Henling and Michael Day for solving the X-ray crystal structure and John Greaves (UCI) for obtaining high-resolution mass spectra. The authors would also like to acknowledge Professors Gary Spessard and Gretchen Hofmeister for helpful discussions and advice.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
PharmaciaUNSPECIFIED
Issue or Number:11
DOI:10.1021/ol025968+
Record Number:CaltechAUTHORS:20170215-135249615
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170215-135249615
Official Citation:Progress toward the Synthesis of Garsubellin A and Related Phloroglucins:  The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core Sarah J. Spessard and Brian M. Stoltz Organic Letters 2002 4 (11), 1943-1946 DOI: 10.1021/ol025968+
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74332
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:15 Feb 2017 22:45
Last Modified:11 Nov 2021 05:26

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