A convenient synthesis of the beraprost intermediate: a useful method for introducing a C3 unit at the benzyl position

Kazuhiro Higuchi; Kazuyuki Sawada; Hisanori Nambu; Takeshi Shogaki; Yasuyuki Kita

doi:10.1021/ol035371+

A convenient synthesis of the beraprost intermediate: a useful method for introducing a C3 unit at the benzyl position

Org Lett. 2003 Oct 2;5(20):3703-4. doi: 10.1021/ol035371+.

Authors

Kazuhiro Higuchi¹, Kazuyuki Sawada, Hisanori Nambu, Takeshi Shogaki, Yasuyuki Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.

PMID: 14507209
DOI: 10.1021/ol035371+

Abstract

[reaction: see text] The Heck reaction is a more efficient and reliable method than previous ones for introducing a C3 unit at the benzyl position for the synthesis of Beraprost. Especially, trialkylated long-chain amines such as (n-C(8)H(17))(3)N and (n-C(12)H(25))(3)N resulted in good yields. This development will be used for the industrial synthesis of Beraprost.

Publication types

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

MeSH terms

Benzyl Compounds / chemistry*
Epoprostenol / analogs & derivatives*
Epoprostenol / chemical synthesis*
Epoprostenol / chemistry

Substances

Benzyl Compounds
beraprost
Epoprostenol