Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units

TETRAHEDRON LETTERS

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Article

Umezawa, Taiki¹  Sato, Akinori¹  Ameda, Yasuto¹  Casalme, Loida O.¹  Matsuda, Fuyuhiko¹ 

[1] Hokkaido Univ, Grad Sch Environm Sci, Div Environm Mat Sci, Sapporo, Hokkaido 0600810, Japan

关键词: Dolastatin 16;    Unusual amino acid;    Total synthesis;    Mannich reaction;    Organocatalyst;   

DOI  :  10.1016/j.tetlet.2014.11.054

来源: Elsevier

【 摘 要 】

A convenient and scalable synthesis of two unusual amino acid units found in dolastatin 16, dolaphenvaline, and dolamethylleuine, is described. Dolastatin 16, which was first isolated from the sea hare Dolabella auricularia by Pettit, exhibits not only strong inhibition of growth for a variety of human cancer cell lines but also potent antifouling activity against the larvae of the barnacle Balanus amphitrite. The key element of the synthesis is an organocatalytic Mannich reaction to construct two contiguous stereocenters in the amino acid units with almost complete enantio- and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free