## Abstract The enantiomers and the racemate of (3__R__,4__S__,1′__E__)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by e
Pheromone Synthesis, CXLIII. Synthesis and Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus BugBiprorulus bibax
✍ Scribed by Mori, Kenji ;Amaike, Masayasu ;Oliver, James E.
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 580 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
(3__S__,4__R__,1′E)‐3,4‐Bis(1′‐butenyl) tetrahydro‐2‐furanol (1) was synthesized from 1,3‐butadiene and maleic anhydride by employing the HLADH‐catalyzed enzymatic oxidation of meso‐diol 2 as the key step, and shown to be identical with the pheromone produced by the dorsal abdominal glands of the male spined citrus bug (Biprorulus bibax).
📜 SIMILAR VOLUMES
## Abstract The racemate of (3__R__,4__S__,1′__E__)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) was synthesized by employing Ireland's ester enolate Claisen rearrangement of (±)‐5 as the key step. The synthesis was efficient enough to provide 23.7 g of (±)‐1 in 41% overall yield based on (±)‐7 (8 s
## Abstract The racemate as well as both the enantiomers of sordidin (1‐ethyl‐3,5,7‐trimethyl‐2,8‐dioxabicyclo[3.2.1])octane were synthesized, and the natural pheromone was shown to be (1__S__,3__R__,5__R__,7__S__)‐(+)‐1.
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