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Stereoselective Total Synthesis of Polyrhacitides A and B
Author(s) -
Yadav J. S.,
Rajendar Goreti
Publication year - 2011
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.201100888
Subject(s) - stereocenter , chemistry , stereoselectivity , aldol reaction , total synthesis , polyketide , stereochemistry , intramolecular force , lactone , bicyclic molecule , wittig reaction , michael reaction , aldol condensation , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , biosynthesis , enzyme
Two aliphatic polyketide natural products, polyrhacitides A and B, have been synthesized in a concise and highly stereoselective manner. The synthesis involved an auxiliary‐based acetate aldol reaction to generate the initial stereogenic center and an iterative Wittig reaction, intramolecular oxa‐Michael addition, and chelation‐controlled reduction reaction as the key steps to generate additional stereocenters. One‐pot acid‐mediated global deprotection and cyclization reactions shape the final bicyclic lactone core.