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Total Syntheses of (+)-Ineleganolide and (-)-Sinulochmodin C.

ABSTRACT: 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.

SUBMITTER: Tuccinardi JP 

PROVIDER: S-EPMC9651135 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Total Syntheses of (+)-Ineleganolide and (-)-Sinulochmodin C.

Tuccinardi Joseph P JP   Wood John L JL  

Journal of the American Chemical Society 20221025 44

Described herein are the first total syntheses of the nor-furanocembranoid natural products (+)-ineleganolide (<b>1</b>) and (-)-sinulochmodin C (<b>2</b>). 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 <i>via</i> a Nozaki-Hiyama-Kishi cyclization and  ...[more]

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