Synlett 2014; 25(2): 157-162
DOI: 10.1055/s-0033-1340160
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions

Shinji Tadano
Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan   Fax: +81(96)3423397   Email: ishikawa@sci.kumamoto-u.ac.jp
,
Hayato Ishikawa*
Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan   Fax: +81(96)3423397   Email: ishikawa@sci.kumamoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 August 2013

Accepted after revision: 27 September 2013

Publication Date:
05 November 2013 (online)

Abstract

Tryptophan-based dimeric diketopiperazine alkaloids such as ditryptophenaline, WIN 64821, naseseazine A, and naseseazine B, exhibit a unique architecture and interesting biological activity. These alkaloids have been the subject of intense study by the synthetic organic chemistry community, and several elegant total syntheses have been discovered, especially using bioinspired strategies. Described herein is a brief overview of these alkaloid syntheses via bioinspired transformations as key steps.

 
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