New Key Building Block for Ixabepilone from R-(-)-Carvone


Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A synthetic approach is described for the transformation of R-(-)-carvone to methyl (2Z,5S,6E)-5-[(tert-butoxycarbonyl)amino]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate, the key building block for the convergent synthesis of the known antitumor macrolactam ixabepilone. The synthetic sequence includes 10 stages, where the key stage is Curtius rearrangement. Optimal conditions have been found for that rearrangement.

About the authors

R. F. Valeev

Ufa Institute of Chemistry, Ufa Federal Research Center

Author for correspondence.
Email: rusl0@yandex.ru
Russian Federation, Ufa, Bashkortostan

G. R. Sunagatullina

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: rusl0@yandex.ru
Russian Federation, Ufa, Bashkortostan

M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: rusl0@yandex.ru
Russian Federation, Ufa, Bashkortostan

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2019 Pleiades Publishing, Ltd.