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Enantioselective Total Synthesis of (+)‐Vittatalactone
Author(s) -
Yadav Jhillu S.,
Yadav Nagendra Nath,
Rao T. Srinivasa,
Reddy B. V. Subba,
Al Khazim Al Ghamdi Ahmad
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.201100354
Subject(s) - enantioselective synthesis , chemistry , desymmetrization , total synthesis , wittig reaction , hydroboration , yield (engineering) , alkylation , stereochemistry , diol , aldol reaction , organic chemistry , catalysis , metallurgy , materials science
An enantioselective asymmetric total synthesis of (+)‐vittatalactone has been accomplished employing enzymatic desymmetrization approach to create two methyl chiral centres. Other key steps involved are Wittig reaction, Evan's asymmetric alkylation, hydroboration, TEMPO‐BAIB‐mediated selective oxidation of 1,3‐diol and lactonization mediated by p ‐toluenesulfonyl chloride. The total synthesis was achieved by a linear synthetic sequence with an overall yield of 11.8 %.