Total synthesis of (R)-telomestatin

  • Org Lett. 2006 Aug 31;8(18):4165-7. doi: 10.1021/ol061793i.
Takayuki Doi  1 ,  Masahito Yoshida ,  Kazuo Shin-ya ,  Takashi Takahashi
Affiliations
  • 1. Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. [email protected]
PMID: 16928100 DOI: 10.1021/ol061793i
Abstract

We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-(t)Bu) moiety using Kelly's method (PPh3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

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