Bioinspired Synthesis of Nortriterpenoid Propindilactone G

A concise bioinspired synthesis of Schisandra nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suárez remote radical functionalization, a ring expansion enabled by a Wagner–Meerwein...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-03, Vol.142 (11), p.5007-5012
Main Authors: Wang, Yu, Chen, Bo, He, Xubiao, Gui, Jinghan
Format: Article
Language:English
Subjects:
Cyclization
Esterification
Oxidation-Reduction
Stereoisomerism
Triterpenes - chemical synthesis
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Summary:A concise bioinspired synthesis of Schisandra nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suárez remote radical functionalization, a ring expansion enabled by a Wagner–Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c00363