Improved biomimetic total synthesis of D,L-stephacidin A

Thomas J Greshock; Robert M Williams

doi:10.1021/ol701845t

Improved biomimetic total synthesis of D,L-stephacidin A

Org Lett. 2007 Oct 11;9(21):4255-8. doi: 10.1021/ol701845t. Epub 2007 Sep 14.

Authors

Thomas J Greshock¹, Robert M Williams

Affiliation

¹ Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.

PMID: 17854197
DOI: 10.1021/ol701845t

Abstract

The direct conversion of beta-hydroxyproline derivatives into 5-hydroxypyrazin-2(1H)-ones under Mitsunobu conditions has been discovered to be a general biomimetic protocol generating IMDA intermediates and has been applied to the concise, biomimetic total syntheses of D,L-stephacidin A and D,L-brevianamide B.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Hydroxyproline / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Pyrazines / chemistry
Stereoisomerism

Substances

Indole Alkaloids
Pyrazines
stephacidin A
Hydroxyproline

Abstract

Publication types

MeSH terms

Substances

Grants and funding