Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 44, Pages 20539-20547Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c09826
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Funding
- Baylor University
- Welch Foundation [AA-006]
- Cancer Prevention and Research Institute of Texas (CPRIT) [R1309]
- NIGMS-NIH [R01GM136759]
- NSF [CHE-1764240]
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This article describes the first total syntheses of the nor-furanocembranoid natural products (+)-ineleganolide and (-)-sinulochmodin C. The synthetic strategy is based on a transannular Michael reaction and a diastereoselective radical cyclization, and discusses the unexpected stereochemical nuances during the evolution and completion of the total synthesis.
Described herein are the first total syntheses of the nor-furanocembranoid natural products (+)-ineleganolide (1) and (-)-sinulochmodin C (2). The synthetic strategy is predicated on a transannular Michael reaction that provides both natural products from a common macrocyclic intermediate and leverages a diastereoselective radical cyclization to furnish a key bicyclic lactone. The latter is further advanced to a macrocyclic precursor via a Nozaki-Hiyama-Kishi cyclization and a one-pot furan oxidation/oxa-Michael cascade. Unexpected stereochemical nuances that guided the evolution and eventual completion of the total synthesis are discussed.
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