Two-step synthesis of (+/-)-stigmolone, the pheromone of Stigmatella aurantiaca

Authors
Epstein, OL Kulinkovich, OG
Citation
Ol. Epstein et Og. Kulinkovich, Two-step synthesis of (+/-)-stigmolone, the pheromone of Stigmatella aurantiaca, TETRAHEDR L, 42(22), 2001, pp. 3757-3758
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
22
Year of publication
2001
Pages
3757 - 3758
Database
ISI
SICI code
0040-4039(20010528)42:22<3757:TSO(TP>2.0.ZU;2-I
Abstract
Racemic stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of myxobacterium Stigmatella aurantiaca, was synthesised in 67% overall yield , using titanium-mediated hydroxycyclopropanation of 2-methyl-5-hexen-2-ol with ethyl isovalerate followed by the base-induced ring opening of the res ulting 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol. (C) 2001 Pub lished by Elsevier Science Ltd.