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Enantioselective construction of the tricyclic core of curcusones A–D via a cross-electrophile coupling approach

Wright, Austin C. and Stoltz, Brian M. (2019) Enantioselective construction of the tricyclic core of curcusones A–D via a cross-electrophile coupling approach. Chemical Science, 10 (45). pp. 10562-10565. ISSN 2041-6520. PMCID PMC6988747. https://resolver.caltech.edu/CaltechAUTHORS:20191008-075046379

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Abstract

Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A–D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of the 5–7–6 carbocyclic core embedded in each member of the curcusone family. Essential to this route is the use of a cross-electrophile coupling strategy, which has not previously been harnessed in the context of natural product synthesis.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/c9sc04127cDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6988747PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2019 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Received 16th August 2019, Accepted 30th September 2019, First published on 1st October 2019. Caltech and the NSF (1800511) are thanked for supplying funding. Dr Scott Virgil is gratefully acknowledged for purification and crystallization expertise. We thank Dr Michael Takase and Dr Lawrence Henling for collecting X-ray crystallographic data. Dr Steven Loskot and Nicholas Hafeman are acknowledged for helpful discussions. There are no conflicts to declare.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
NSFCHE-1800511
Issue or Number:45
PubMed Central ID:PMC6988747
Record Number:CaltechAUTHORS:20191008-075046379
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20191008-075046379
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:99133
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:08 Oct 2019 16:35
Last Modified:18 Feb 2020 17:27

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