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Pheromone Synthesis, CLVIII. New Synthesis and Revision of the Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus BugBiprorulus bibax

✍ Scribed by Mori, Kenji ;Amaike, Masayasu ;Watanabe, Hidenori

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
901 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 employing either chemical asymmetric reduction [12 → (S)‐8b] or lipase‐mediated asymmetric hydrolysis (9→10) and acetylation (meso‐2 → ent‐10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3__R__,4__S__) on the basis of the chemical asymmetric synthesis of (3__S__,4__R__)‐3 by starting from (S)‐8b of known stereochemistry.

📜 SIMILAR VOLUMES

Pheromone Synthesis, CXLIII. Synthesis a
Pheromone Synthesis, CXLIII. Synthesis and Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus BugBiprorulus bibax
✍ Mori, Kenji ;Amaike, Masayasu ;Oliver, James E. 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 580 KB

## 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 abdom

Pheromone synthesis CLXIX. Improved synt
Pheromone synthesis CLXIX. Improved synthesis of the racemate of the hemiacetal pheromone of the spined citrus bugBiprorulus bibax
✍ Amaike, Masayasu ;Mori, Kenji 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 360 KB

## 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

Pheromone Synthesis, CLXXXIV. Synthesis
Pheromone Synthesis, CLXXXIV. Synthesis and Absolute Configuration of Sordidin, the Male-Produced Aggregation Pheromone of the Banana Weevil,cosmopolites sordidus
✍ Nakayama, T??Ru ;Mori, Kenji 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 666 KB

## 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.

ChemInform Abstract: Pheromone Synthesis
ChemInform Abstract: Pheromone Synthesis. Part 184. Synthesis and Absolute Configuration of Sordidin, the Male-Produced Aggregation Pheromone of the Banana Weevil, Cosmopolites sordidus.
✍ T. NAKAYAMA; K. MORI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v