Abstract
(2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.
| Original language | English |
|---|---|
| Pages (from-to) | 11421-11430 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 54 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - 1998 Sep 17 |
| Externally published | Yes |
Keywords
- Olefination
- Pheromones
- Sulfur compound
- Terpenes and terpenoids
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Kuwahara, S., Itoh, D., Leal, W. S., & Kodama, O. (1998). A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula). Tetrahedron, 54(38), 11421-11430. https://doi.org/10.1016/S0040-4020(98)00696-6