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Total Syntheses of (+)-Peniciketals A-B and (-)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol.

ABSTRACT: A late-stage photoisomerization/cyclization union tactic, in conjunction with Type I Anion Relay Chemistry (ARC), permits enantioselective total syntheses and then biological evaluation of (+)-peniciketals A and B. The photochemical protocol was further showcased by an efficient three-step construction of the architecturally complex polycyclic skeleton found in (-)-diocollettines A. The mechanism and diastereoselectivity of the photochemical protocol have also been explored by both experiment and density functional theory calculations.

SUBMITTER: Deng Y

PROVIDER: S-EPMC8730323 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Total Syntheses of (+)-Peniciketals A-B and (-)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol.

Deng Yifan Y Zou Yike Y Yang Chia-Ping H CH Houk K N KN Smith Amos B AB

The Journal of organic chemistry 20210912 19

A late-stage photoisomerization/cyclization union tactic, in conjunction with Type I Anion Relay Chemistry (ARC), permits enantioselective total syntheses and then biological evaluation of (+)-peniciketals A and B. The photochemical protocol was further showcased by an efficient three-step construction of the architecturally complex polycyclic skeleton found in (-)-diocollettines A. The mechanism and diastereoselectivity of the photochemical protocol have also been explored by both experiment an ...[more]

PMID: 34510901

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