Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 22nd May 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.

Issue 8, 2013
Previous Article Next Article

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

Author affiliations


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

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Apr 2013, accepted on 29 May 2013 and first published on 29 May 2013

Article type: Edge Article
DOI: 10.1039/C3SC51150B
Chem. Sci., 2013,4, 3191-3197

  •   Request permissions

    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

Search articles by author