Total Synthesis of LeucosceptroidsA and B

LeucosceptroidsA and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroidB and the first total synthesis of leucosceptroidA are presented. The key transformations include an aldol reaction between a substituted dihydr...

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Bibliographic Details
Published in:Angewandte Chemie 2015-01, Vol.127 (4), p.1314-1317
Main Authors: Guo, Sheng, Liu, Jie, Ma, Dawei
Format: Article
Language:eng ; ger
Subjects:
Alcohols
Aldehydes
Chemistry
Oxidation
Radicals
Synthesis
Transformations
Online Access:Get full text
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Summary:LeucosceptroidsA and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroidB and the first total synthesis of leucosceptroidA are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)-citronellal-derived aldehyde, a SmI2-mediated intramolecular ketyl-olefin radical cyclization, and final-stage alcohol oxidation.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201410134