Published December 7, 2019
| Published + Supplemental Material
Journal Article
Open
Enantioselective construction of the tricyclic core of curcusones A–D via a cross-electrophile coupling approach
- Creators
- Wright, Austin C.
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Stoltz, Brian M.
Chicago
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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.
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.Attached Files
Published - c9sc04127c.pdf
Supplemental Material - c9sc04127c1_si.pdf
Supplemental Material - c9sc04127c2.cif
Supplemental Material - c9sc04127c3.cif
Files
c9sc04127c.pdf
Additional details
- PMCID
- PMC6988747
- Eprint ID
- 99133
- Resolver ID
- CaltechAUTHORS:20191008-075046379
- Caltech
- NSF
- CHE-1800511
- Created
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2019-10-08Created from EPrint's datestamp field
- Updated
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2022-02-16Created from EPrint's last_modified field