Total Synthesis of Leucosceptroids A and B

Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram‐scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dih...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-01, Vol.54 (4), p.1298-1301
Main Authors: Guo, Sheng, Liu, Jie, Ma, Dawei
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
aldol reaction
Alkenes - chemistry
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Catalysis
Colletotrichum - drug effects
Crystallography, X-Ray
Cyclization
Free Radicals - chemistry
Iodides - chemistry
Molecular Conformation
natural products
Rhizoctonia - drug effects
Samarium - chemistry
Sesterterpenes - chemical synthesis
Sesterterpenes - chemistry
Sesterterpenes - pharmacology
sesterterpenoids
total synthesis
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Summary:Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram‐scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A 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. The sesterterpenoids leucosceptroids A and B are plant secondary metabolites with potent antifeedant and antifungal activities. A convergent and scalable synthesis of leucosceptroids A and B was achieved by employing an aldol reaction and an SmI2‐mediated intramolecular ketyl–olefin radical cyclization as the key steps.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201410134