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Stereoselective Total Syntheses of Acutifolone A, Bisacutifolone A and B, Pinguisenol, and Isonaviculol.

ABSTRACT: Stereoselective total syntheses of pinguisane type of sesquiterpenoids are described following a unified approach using a chiral building block derived from (R)-pulegone. The functionality embodied in the key intermediate enables their facile elaboration into more complex structures of biological relevance such as acutifolone A (9 steps, 22% overall yield) and bisacutifolone A and B (6 and 8%, respectively) following Furukawa's modified Simmons-Smith cyclopropanation, Luche reduction, Saegusa-Ito oxidation, pyridinium chlorochromate-mediated 1,3-oxidative transposition, and Diels-Alder dimerization as key steps.

SUBMITTER: Yadav JS

PROVIDER: S-EPMC6641225 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Stereoselective Total Syntheses of Acutifolone A, Bisacutifolone A and B, Pinguisenol, and Isonaviculol.

Yadav Jhillu Singh JS Singh Shweta S Das Saibal S

ACS omega 20180119 1

Stereoselective total syntheses of pinguisane type of sesquiterpenoids are described following a unified approach using a chiral building block derived from (<i>R</i>)-pulegone. The functionality embodied in the key intermediate enables their facile elaboration into more complex structures of biological relevance such as acutifolone A (9 steps, 22% overall yield) and bisacutifolone A and B (6 and 8%, respectively) following Furukawa's modified Simmons-Smith cyclopropanation, Luche reduction, Sae ...[more]

PMID: 31457920

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