Asymmetric Synthesis of Axinellamines A and B

Zhiqiang Ma; Xiao Wang; Yuyong Ma; Chuo Chen

doi:10.1002/anie.201600007

Asymmetric Synthesis of Axinellamines A and B

Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4763-6. doi: 10.1002/anie.201600007. Epub 2016 Mar 8.

Authors

Zhiqiang Ma¹, Xiao Wang^{1

2}, Yuyong Ma^{1

2}, Chuo Chen³

Affiliations

¹ Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX, 75390, USA.
² Department of Chemistry and Biochemistry, The University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA.
³ Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX, 75390, USA. [email protected].

Abstract

Axinellamines A and B are broad-spectrum antibacterial pyrrole-imidazole alkaloids that have a complex polycyclic skeleton. A new asymmetric synthesis of these marine sponge metabolites is described herein, featuring an oxidative rearrangement and an anchimeric chlorination reaction.

Keywords: alkaloids; anchimeric assistance; axinellamines; natural products; total synthesis.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Imidazoles / chemical synthesis*
Isomerism
Pyrroles / chemical synthesis*

Substances

Imidazoles
Pyrroles
axinellamine

Abstract

Publication types

MeSH terms

Substances

Grants and funding