Unsaturated carbohydrates. Part 27. Synthesis of (–)-exo-brevicomin from a nona-3,8-dienulose derivative
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 301-303
- https://doi.org/10.1039/p19850000301
Abstract
The (–)-enantiomer (11) of the insect pheromone (+)-exo-brevicomin has been synthesized directly by hydrogenation–hydrogenolysis of the L-lyxo-nona-3,8-dienulose derivative (10). Epoxide ring opening of the methyl 3,4-anhydro-D-galactopyranoside (6), which was readily obtained from methyl α-D-glucopyranoside, permitted the required configurational inversions at C-3 and C-4This publication has 3 references indexed in Scilit:
- Convenient synthetic route to 6,8-dioxabicyclo[3.2.1]octanes, the aggregation pheromone components of bark beetlesJournal of the Chemical Society, Perkin Transactions 1, 1983
- Unsaturated carbohydrates. Part 25. Abbreviated synthesis of the insect pheromone (+)-exo-brevicomin from a nona-3,8-dienulose derivativeJournal of the Chemical Society, Perkin Transactions 1, 1983
- Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. 2. Synthesis of (+)-exo-brevicominThe Journal of Organic Chemistry, 1982