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Studies Directed Towards the Total Synthesis of (–)‐Dictyostatin
Author(s) -
Yadav Jhillu S.,
Rajender Vemula
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901448
Subject(s) - desymmetrization , chemistry , stille reaction , sonogashira coupling , stereochemistry , aldol reaction , total synthesis , stereoselectivity , enantioselective synthesis , combinatorial chemistry , diene , palladium , organic chemistry , catalysis , natural rubber
The stereoselective synthesis of the three major fragments (C1–C9, C10–C17, and C19–C26) of an antimitotic marine macrolide, (–)‐dictyostatin, has been achieved with a desymmetrization strategy and Oppolzer syn and anti aldol protocols as the key reactions. Takai olefination and Sonogashira coupling reactions were successfully utilized to establish the 2 Z ,4 E ‐dienoate portion of the C1–C9 fragment and Stille coupling for the Z ‐diene core of C19–C26.
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