A concise synthesis of the molecular framework of pleuromutilin

Two syntheses of the tricyclic carbon skeleton of pleuromutilin are reported. Diastereoselective 1,4-conjugate additions were used to elaborate bicyclic precursors at an early stage of each route, while ring-forming olefin metatheses were executed to complete the pleuromutilin carbon framework. The...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (5), p.1500-1502
Main Authors: Liu, Junjia, Lotesta, Stephen D, Sorensen, Erik J
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Carbon
Congeners
Diterpenes - chemical synthesis
Diterpenes - chemistry
Models, Chemical
Molecular Structure
Olefins
Pleuromutilins
Polycyclic Compounds
Precursors
Stereoisomerism
Synthesis
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Summary:Two syntheses of the tricyclic carbon skeleton of pleuromutilin are reported. Diastereoselective 1,4-conjugate additions were used to elaborate bicyclic precursors at an early stage of each route, while ring-forming olefin metatheses were executed to complete the pleuromutilin carbon framework. The congeners prepared are appropriately functionalized to enable access to diverse pleuromutilin analogues.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc04077k