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Asymmetric Total Synthesis of Amphirionin-2.

Authors :
Saha D
Mandal GH
Goswami RK
Source :
The Journal of organic chemistry [J Org Chem] 2021 Aug 06; Vol. 86 (15), pp. 10006-10022. Date of Electronic Publication: 2021 Jul 16.
Publication Year :
2021

Abstract

A convergent route for the asymmetric total synthesis of potent anticancer polyketide natural product amphirionin-2 has been developed. Our initial synthetic trials revealed that the proposed structures of amphirionin-2 need to be revised consistent with a recent report of Fuwa et al., where the actual structure of amphirionin-2 was established. The key features of our synthesis comprised Sharpless asymmetric dihydroxylation, followed by cycloetherification, Wittig olefination, Julia-Kocienski olefination, and Crimmins propionate aldol reaction.

Details

Language :
English
ISSN :
1520-6904
Volume :
86
Issue :
15
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
34269065
Full Text :
https://doi.org/10.1021/acs.joc.1c00686