Glycal approach to the synthesis of macrolide (−)-A26771B

A convergent total synthesis of a 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri- O -acetyl- d -glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7 , cross metathesis between chiral fragments 3 and 4 , Yamaguchi macrolactonization and selective oxid...

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Bibliographic Details
Published in:RSC advances 2015-01, Vol.5 (37), p.29114-29120
Main Authors: Saidhareddy, Puli, Shaw, Arun K.
Format: Article
Language:English
Subjects:
Alcohols
Decomposition reactions
Fragments
Metathesis
Natural products
Oxidation
Synthesis
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Summary:A convergent total synthesis of a 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri- O -acetyl- d -glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7 , cross metathesis between chiral fragments 3 and 4 , Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA17084A