Title: Methyl (3 R,5 R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of ( )-(3 R,5 R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether.
Authors: Mineeva, I.
Abstract: A simple and efficient asymmetric synthesis of (5 S,7 R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of ( )-(3 R,5 R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3 R,5 R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.
Subjects: ASYMMETRY (Chemistry); CHEMICAL synthesis; PHEROMONES; LACTONES; ALLYLATION
Publication: Russian Journal of Organic Chemistry, 2013, Vol 49, Issue 6, p838
ISSN: 1070-4280
Publication type: Academic Journal
DOI: 10.1134/S1070428013060067

Methyl (3 R,5 R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of ( )-(3 R,5 R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether.

Mineeva, I.