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Issue 20, 2012
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Formal total synthesis of (−)-exiguolide

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The formal total synthesis of (−)-exiguolide through the chiral-pool approach is described. The key reactions involved for formation of the macrocyclic core from two subunits are Julia–Kocienski olefination and Yamaguchi macrolactonization. The major methylene bis-tetrahydropyran fragment was achieved in a convergent manner from L-glutamic acid and L-aspartic acid involving the oxa-Michael reaction and an aldol-driven reductive etherification as key steps for the formation of a tetrahydropyran ring. The other sulfone subunit was prepared via an Evans aldol reaction.

Graphical abstract: Formal total synthesis of (−)-exiguolide

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Publication details

The article was received on 11 Jun 2012, accepted on 12 Jun 2012 and first published on 22 Jun 2012

Article type: Paper
DOI: 10.1039/C2RA21161K
RSC Adv., 2012,2, 7724-7734

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    Formal total synthesis of (−)-exiguolide

    C. R. Reddy and N. N. Rao, RSC Adv., 2012, 2, 7724
    DOI: 10.1039/C2RA21161K

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