Jump to main content
Jump to site search

Issue 20, 2012
Previous Article Next Article

Formal total synthesis of (−)-exiguolide

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

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

  •   Request permissions

    Formal total synthesis of (−)-exiguolide

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

Search articles by author

Spotlight

Advertisements