Total synthesis of (R)-telomestatin

Takayuki Doi; Masahito Yoshida; Kazuo Shin-ya; Takashi Takahashi

doi:10.1021/ol061793i

Total synthesis of (R)-telomestatin

Org Lett. 2006 Aug 31;8(18):4165-7. doi: 10.1021/ol061793i.

Authors

Takayuki Doi¹, Masahito Yoshida, Kazuo Shin-ya, Takashi Takahashi

Affiliation

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure
Oxazoles / chemical synthesis*
Streptomyces / chemistry
Telomerase / antagonists & inhibitors

Substances

Oxazoles
telomestatin
Telomerase