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A divergent enantioselective strategy for the synthesis of griseusins.

ABSTRACT: The first enantioselective total synthesis of griseusin?A, griseusin?C, 4'-deacetyl-griseusin?A, and two non-native counterparts in 11-14 steps is reported. This strategy highlights a key hydroxy-directed C?H olefination of 1-methylene isochroman with an ?,?-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cyclization to afford the signature tetrahydro-spiropyran ring. Colorectal cancer cell cytotoxicities of the final products highlight the impact of the griseusin tetrahydro-spiropyran ring on bioactivity. As the first divergent enantioselective synthesis, the strategy put forth sets the stage for further griseusin mechanism-of-action and SAR studies.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC4565752 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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A divergent enantioselective strategy for the synthesis of griseusins.

Zhang Yinan Y Ye Qing Q Wang Xiachang X She Qing-Bai QB Thorson Jon S JS

Angewandte Chemie (International ed. in English) 20150731 38

The first enantioselective total synthesis of griseusin A, griseusin C, 4'-deacetyl-griseusin A, and two non-native counterparts in 11-14 steps is reported. This strategy highlights a key hydroxy-directed CH olefination of 1-methylene isochroman with an α,β-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cyclization to afford the signature tetrahydro-spiropyran ring. Colorectal cancer cell cytotoxicities of the final products highlight the impact of the ...[more]

PMID: 26230189

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