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Total Synthesis of the Diterpene Waihoensene.

ABSTRACT: A racemic and scalable enantioselective total synthesis of (+)-waihoensene was accomplished. (+)-Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all-cis-fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson-Khand reaction, a diastereoselective ?-alkylation, and a diastereoselective 1,4-addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale.

SUBMITTER: Rosenbaum LC

PROVIDER: S-EPMC7898921 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Total Synthesis of the Diterpene Waihoensene.

Rosenbaum Lisa-Catherine LC Häfner Maximilian M Gaich Tanja T

Angewandte Chemie (International ed. in English) 20201210 6

A racemic and scalable enantioselective total synthesis of (+)-waihoensene was accomplished. (+)-Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all-cis-fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson-Khand reaction, a ...[more]

PMID: 33103334

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