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. 2013 Jan 1;69(2):770-773.
doi: 10.1016/j.tet.2012.10.075.

Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative, Late-Stage Biosynthetic Intermediate

Timothy R Welch  1 , Robert M Williams  2
Affiliations

Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative, Late-Stage Biosynthetic Intermediate

Timothy R Welch et al. Tetrahedron. .

Abstract

The enantiospecific synthesis of desthiochetomin, a putative biosynthetic intermediate of the epidithiodioxopiperazine natural product chetomin, is described. A diastereoselective N-alkylation was employed to form the key C3-N1' bond of the heterodimeric indoline core, followed by peptide coupling and dioxopiperazine cyclization with the requisite N-methyl amino acids. A related sarcosine-derived dioxopiperazine was prepared in the same manner. The first proposed biosynthesis of chetomin is also detailed in the text.

Keywords: Aspergillus versicolor; biosynthesis; prenylated indole alkaloid.

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Figures

Figure 1
Figure 1
Structures of chetomin, gliotoxin and sirodesmin PL.
Scheme 1
Scheme 1
Proposed biosynthesis of chetomin.
Scheme 2
Scheme 2
Synthesis of postulated biosynthetic intermediate 7.
Scheme 3
Scheme 3
Synthesis of sarcosine-derived dioxopiperazine.
See this image and copyright information in PMC

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