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Issue 8, 2013
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Concise total synthesis of (+)-bionectins A and C

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Abstract

The concise and efficient total synthesis of (+)-bionectins A and C is described. Our approach to these natural products features a new and scalable method for erythro-β-hydroxytryptophan amino acid synthesis, an intramolecular Friedel–Crafts reaction of a silyl-tethered indole, and a new mercaptan reagent for epipolythiodiketopiperazine (ETP) synthesis that can be unravelled under very mild conditions. In evaluating the impact of C12-hydroxylation, we have identified a unique need for an intramolecular variant of our Friedel–Crafts indolylation chemistry. Several key discoveries including the first example of permanganate-mediated stereoinvertive hydroxylation of the α-stereocenters of diketopiperazines as well as the first example of a direct triketopiperazine synthesis from a parent cyclo-dipeptide are discussed. Finally, the synthesis of (+)-bionectin A and its unambiguous structural assignment through X-ray analysis provides motivation for the reevaluation of its original characterization data and assignment.

Graphical abstract: Concise total synthesis of (+)-bionectins A and C

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Supplementary files

Article information


Submitted
28 Apr 2013
Accepted
29 May 2013
First published
29 May 2013

Chem. Sci., 2013,4, 3191-3197
Article type
Edge Article

Concise total synthesis of (+)-bionectins A and C

A. Coste, J. Kim, T. C. Adams and M. Movassaghi, Chem. Sci., 2013, 4, 3191
DOI: 10.1039/C3SC51150B

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