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

Jhillu S. Yadav; Tenneti Srinivasa Rao; Nagendra Nath Yadav; Kovvuru V. Raghavendra Rao; Basi V. Subba Reddy; Ahmad Al Khazim Al Ghamdi

doi:10.1055/s-0031-1289699

PAPER

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

Jhillu S. Yadav*^a, Tenneti Srinivasa Rao^a, Nagendra Nath Yadav^a, Kovvuru V. Raghavendra Rao^a, Basi V. Subba Reddy^a, Ahmad Al Khazim Al Ghamdi^b
^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

Abstract

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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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