2011European Journal of Organic ChemistryRequires access

Enantioselective Total Synthesis of (+)‐Vittatalactone

J. S. Yadav, Nagendra Nath Yadav, T. Srinivasa Rao, B. V. Subba Reddy, Ahmad Al Khazim Al Ghamdi

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Abstract

Abstract 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 %.

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Abstract 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 %.

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Available abstract

Abstract 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 %.

Key concepts: Enantioselective synthesis, Chemistry, Desymmetrization, Total synthesis, Wittig reaction, Hydroboration, Yield (engineering), Alkylation

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