Synthesis and Reactions of the Pestalotiopsin Skeleton

Family ties: The pestalotiopsin framework has been constructed by using a SmI2‐mediated cyclization and a Nozaki–Hiyama–Kishi coupling to construct the four‐ and nine‐membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural pro...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2008-07, Vol.47 (30), p.5631-5633
Main Authors: Baker, Thomas M., Edmonds, David J., Hamilton, Deborah, O'Brien, Christopher J., Procter, David J.
Format: Article
Language:English
Subjects:
Cyclization
Magnetic Resonance Spectroscopy
Molecular Structure
natural products
pestalotiopsins
samarium
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
taedolidols
total synthesis
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Summary:Family ties: The pestalotiopsin framework has been constructed by using a SmI2‐mediated cyclization and a Nozaki–Hiyama–Kishi coupling to construct the four‐ and nine‐membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid‐mediated cyclization of the pestalotiopsin skeleton.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801900