Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions

Shinji Tadano; Hayato Ishikawa

doi:10.1055/s-0033-1340160

Synlett, Table of Contents

Synlett 2014; 25(2): 157-162
DOI: 10.1055/s-0033-1340160

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Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions

Authors

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

Abstract

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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.

Key words

alkaloids - biosynthesis - bioinspired reaction - dimerization - tryptophan dimers - indoles

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References

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