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. doi:10.1039/c9sc04127c. 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.
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| 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. | |||||||||
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| Issue or Number: | 45 | |||||||||
| PubMed Central ID: | PMC6988747 | |||||||||
| DOI: | 10.1039/c9sc04127c | |||||||||
| 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: | 16 Feb 2022 00:49 |
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