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

J. S. Yadav | Zendy; Shweta Singh | Zendy; Saibal Das | Zendy

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

Author(s) -

J. S. Yadav,

Shweta Singh,

Saibal Das

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01513

Subject(s) - stereoselectivity , pyridinium chlorochromate , chemistry , stereochemistry , total synthesis , yield (engineering) , cyclopropanation , organic chemistry , catalysis , materials science , metallurgy

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.

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