Total synthesis of (-)-serotobenine

Yasuaki Koizumi; Hideki Kobayashi; Toshiyuki Wakimoto; Takumi Furuta; Tohru Fukuyama; Toshiyuki Kan

doi:10.1021/ja807676v

Total synthesis of (-)-serotobenine

J Am Chem Soc. 2008 Dec 17;130(50):16854-5. doi: 10.1021/ja807676v.

Authors

Yasuaki Koizumi¹, Hideki Kobayashi, Toshiyuki Wakimoto, Takumi Furuta, Tohru Fukuyama, Toshiyuki Kan

Affiliation

¹ School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

PMID: 19053440
DOI: 10.1021/ja807676v

Abstract

The efficient total synthesis of (-)-serotobenine (1) has been achieved by constructing an optically active dihydrobenzofuran ring via a rhodium carbenoid mediated intramolecular C-H insertion reaction, which was developed by our group. Then the possibility of racemization of 1 was investigated using optically active synthetic 1.

Publication types

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

MeSH terms

Benzofurans / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Isomerism
Molecular Structure

Substances

Benzofurans
Indoles
serotobenine