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Formal Total Synthesis of Palmerolide A
Author(s) -
Pawar Amit B.,
Prasad Kavirayani R.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202324
Subject(s) - desymmetrization , stille reaction , total synthesis , metathesis , tartaric acid , amide , chemistry , ring closing metathesis , stereochemistry , formal synthesis , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , polymer , citric acid , polymerization
A formal total synthesis of the 20‐membered marine macrolide, palmerolide A from chiral pool tartaric acid is described. Elaboration of a γ‐hydroxy amide, which is derived from the desymmetrization of tartaric acid amide, and Boord olefination are the pivotal reactions employed for the synthesis of the chiral building blocks, and Stille coupling and ring‐closing metathesis (RCM) are used to assemble the macrolactone.