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Synthesis 2012(5): 788-792  
DOI: 10.1055/s-0031-1289699
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoenzymatic Approach to the Total Synthesis of (+)-Bourgeanic Acid

Jhillu S. Yadav*a, Tenneti Srinivasa Raoa, Nagendra Nath Yadava, Kovvuru V. Raghavendra Raoa, Basi V. Subba Reddya, Ahmad Al Khazim Al Ghamdib
a Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b Engineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia
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Publikationsverlauf

Received 11 October 2011
Publikationsdatum:
10. Februar 2012 (online)

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Abstract

A highly stereoselective total synthesis of (+)-bourgeanic acid has been accomplished by an enzymatic desymmetrization approach to create two methyl chiral centers. Other key steps involved in this approach are a Wittig reaction, a Gilman reaction, and TEMPO/iodobenzene diacetate mediated selective oxidation of the 1,3-diol, Yamaguchi lactonization and lithium hydroxide mediated partial hydrolysis (saponification) of the eight-membered cyclic dilactone

Key words

enzymatic desymmetrization - aliphatic depside - (+)-bourgeanic acid - bourgeanic lactone - (-)-hemibourgeanic acid - Wittig reaction - Gilman reaction - Yamaguchi lactonization

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