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Published on: April 4, 2014
Total Syntheses of (+)-Peniciketals A-B and (-)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union
Yifan Deng1, Yike Zou2, Chia-Ping H Yang3
1Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
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.
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