|
|||||
|
|
Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one |
|
| Authors: | Helen C Hailes Ben Isaac M Hashim Javaid |
| Institution: | a Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK b Bush Boake Allen Ltd, Blackhorse Lane, London E17 5QP, UK |
| Abstract: | A novel and efficient synthesis of both (±)-methyl epijasmonate and (±)-cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one is described. The key step to establish the cis-stereochemistry on the 5-membered ring is an ionic Diels–Alder reaction, which is high yielding and highly regioselective. Subsequent key steps include oxidative cleavage of the six-membered ring, Wittig coupling and for the synthesis of epijasmonate, the haloform reaction. |
| Keywords: | jasmonates ionic Diels–Alder haloform reaction |
| 本文献已被 ScienceDirect 等数据库收录！ | |