Enantioselective Total Syntheses of the Cephalotaxus Alkaloids (−)-Fortuneicyclidins A and B and (−)-Cephalotine B

Enantioselective Total Syntheses of the Cephalotaxus Alkaloids (−)-Fortuneicyclidins A and B and (−)-Cephalotine B

Fortuneicyclidins A and B are a pair of recently isolated Cephalotaxus alkaloids with an unprecedented rearranged polycyclic skeleton possessing multiple complex stereocenters and functionalization. In this work, highly stereocontrolled asymmetric total syntheses for title alkaloids were outlined. K...

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Veröffentlicht in:Organic letters 2023-10, Vol.25 (41), p.7464-7469
Hauptverfasser: Sheng, Peng-Zhen, Ni, Zhi-Bin, Li, Lu-Lu, Wei, Kun, Zhang, Hongbin, Yang, Yu-Rong
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container_end_page 7469
container_issue 41
container_start_page 7464
container_title Organic letters
container_volume 25
creator Sheng, Peng-Zhen
Ni, Zhi-Bin
Li, Lu-Lu
Wei, Kun
Zhang, Hongbin
Yang, Yu-Rong
description Fortuneicyclidins A and B are a pair of recently isolated Cephalotaxus alkaloids with an unprecedented rearranged polycyclic skeleton possessing multiple complex stereocenters and functionalization. In this work, highly stereocontrolled asymmetric total syntheses for title alkaloids were outlined. Key features include an underexplored Ir-catalyzed α-allylation of aldehyde to strategically install a vicinal N-substituted quaternary center and a tertiary stereocenter, Heck and RCM reactions to construct the critical polycyclic framework rapidly, two different tandem oxidation–transannular aldol cyclization processes, one through ozonolysis and another via Swern oxidation, to forge the last ring for fortuneicyclidins A and B, respectively. In this approach, the challenging C-2 hydroxyl group can be installed stereospecifically.
doi_str_mv 10.1021/acs.orglett.3c02739
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title Enantioselective Total Syntheses of the Cephalotaxus Alkaloids (−)-Fortuneicyclidins A and B and (−)-Cephalotine B
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