Issue 2, 2018

Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

Abstract

The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described. A critical aspect of our expedient route was the development of a directed regio- and diastereoselective C3–N1′ coupling of complex tetracyclic diketopiperazine components. This late-stage heterodimerization reaction was made possible by design of tetracyclic diketopiperazines that allow C3-carbocation coupling of the electrophilic component to the N1′ locus of the nucleophilic fragment. The application of this new coupling reaction to the first total synthesis of (+)-asperazine A led to our revision of the sign and magnitude of the optical rotation for the reported structure.

Graphical abstract: Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

Supplementary files

Article information

Article type
Communication
Submitted
19 Oct 2017
Accepted
04 Dec 2017
First published
08 Dec 2017

Org. Biomol. Chem., 2018,16, 202-207

Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

B. M. Nelson, R. P. Loach, S. Schiesser and M. Movassaghi, Org. Biomol. Chem., 2018, 16, 202 DOI: 10.1039/C7OB02985C

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