（+）- yatakemycin的全合成。

Total synthesis of (+)-yatakemycin.

作者信息

Okano Kentaro, Tokuyama Hidetoshi, Fukuyama Tohru

机构信息

Graduate School of Pharmaceutical Sciences, University of Tokyo, PRESTO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

出版信息

J Am Chem Soc. 2006 Jun 7;128(22):7136-7. doi: 10.1021/ja0619455.

DOI:10.1021/ja0619455

PMID:16734447

Abstract

A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.

摘要

通过20步反应完成了（+）-yatakemycin的汇聚式全合成，总收率为13%。该合成的特点包括：（S）-环氧氯丙烷与2,6-二溴苯基锂进行区域选择性开环反应；使用碘化亚铜和醋酸铯组合进行温和的铜介导芳基胺化反应；在五甲基苯存在下，用三氯化硼高效脱除芳基苄基醚的苄基。