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Stereoselective Total Synthesis of 4‐Ketoclonostachydiol
Author(s) -
Rajaram Singanaboina,
Ramulu Udugu,
Ramesh Dasari,
Prabhakar Peddikotla,
Venkateswarlu Yenamandra
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200631
Subject(s) - chemistry , stereoselectivity , kinetic resolution , total synthesis , ring closing metathesis , metathesis , hydroxylation , epoxide , grignard reaction , stereochemistry , hydrolysis , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , enzyme , reagent , polymer , polymerization
An efficient stereoselective total synthesis of the bioactive 14‐membered natural macrocyclic bislactone 4‐ketoclonostachydiol is described. The strategy involves a Jacobsen 's hydrolytic kinetic resolution (HKR), epoxide opening, MacMillan α ‐hydroxylation, Horner Wadsworth Emmons olefination, a Grignard reaction, and Hoveyda Grubbs ‐ II ‐catalyzed ring‐closing metathesis (RCM) as key steps.