Jump to main content
Jump to site search

Issue 6, 2012
Previous Article Next Article

Concise total synthesis of (+)-gliocladins B and C

Author affiliations

Abstract

The first total synthesis of (+)-gliocladin B is described. Our concise and enantioselective synthesis takes advantage of a new regioselective Friedel–Crafts-based strategy to provide an efficient multigram-scale access to the C3-(3′-indolyl)hexahydropyrroloindole substructure, a molecular foundation present in a significant subset of epipolythiodiketopiperazine natural alkaloids. Our first-generation solution to (+)-gliocladin B involved the stereoselective formation of (+)-12-deoxybionectin A, a plausible biosynthetic precursor. Our synthesis clarified the C15 stereochemistry of (+)-gliocladin B and allowed its full structure confirmation. Further studies of a versatile dihydroxylated diketopiperazine provided a concise and efficient synthesis of (+)-gliocladin B as well as access to (+)-gliocladin C.

Graphical abstract: Concise total synthesis of (+)-gliocladins B and C

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 05 Mar 2012, accepted on 30 Mar 2012 and first published on 30 Mar 2012


Article type: Edge Article
DOI: 10.1039/C2SC20270K
Citation: Chem. Sci., 2012,3, 1798-1803
  •   Request permissions

    Concise total synthesis of (+)-gliocladins B and C

    N. Boyer and M. Movassaghi, Chem. Sci., 2012, 3, 1798
    DOI: 10.1039/C2SC20270K

Search articles by author