Preparing functional bis(indole) pyrazine by stepwise cross-coupling reactions: an efficient method to construct the skeleton of dragmacidin D

Cai-Guang Yang; Gang Liu; Biao Jiang

doi:10.1021/jo026450m

Preparing functional bis(indole) pyrazine by stepwise cross-coupling reactions: an efficient method to construct the skeleton of dragmacidin D

J Org Chem. 2002 Dec 27;67(26):9392-6. doi: 10.1021/jo026450m.

Authors

Cai-Guang Yang¹, Gang Liu, Biao Jiang

Affiliation

¹ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China.

PMID: 12492343
DOI: 10.1021/jo026450m

Abstract

A direct approach for selective construction of properly substituted bis(indole) pyrazine, the skeleton of a marine alkaloid dragmacidin D, has been developed. The key steps involved the regioselective introduction of two indole units, using the palladium(0)-catalyzed Suzuki and the Stille cross-coupling reactions sequentially.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Animals
Catalysis
Combinatorial Chemistry Techniques*
Hydrocarbons, Brominated / chemical synthesis*
Indole Alkaloids
Indoles / chemical synthesis*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Palladium / chemistry*
Piperazines / chemical synthesis*
Porifera / chemistry
Pyrazines / chemical synthesis*

Substances

Alkaloids
Hydrocarbons, Brominated
Indole Alkaloids
Indoles
Piperazines
Pyrazines
dragmacidin D
Palladium