PHEROMONES OF COLEOPTERA .13. SYNTHESIS OF RACEMIC FERRULACTONE-II FROM 3 EASILY ACCESSIBLE ACETYLENIC PRECURSORS

Authors
MAVROV MV SEREBRYAKOV EP
Citation
Mv. Mavrov et Ep. Serebryakov, PHEROMONES OF COLEOPTERA .13. SYNTHESIS OF RACEMIC FERRULACTONE-II FROM 3 EASILY ACCESSIBLE ACETYLENIC PRECURSORS, Russian chemical bulletin, 42(12), 1993, pp. 2035-2038
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
42
Issue
12
Year of publication
1993
Pages
2035 - 2038
Database
ISI
SICI code
1066-5285(1993)42:12<2035:POC.SO>2.0.ZU;2-W
Abstract
A ten-step synthesis of a racemic form of 3(Z),11(S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Ca diot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol fo llowed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). Air of the three building blocks used for the chain assembly are easily ac cessible from acetylene. The protection of OH groups as tert-butyl eth ers has certain synthetic advantages.