Enzymatic preparation of (4R,6R)-4-hydroxy-1,7-dioxaspiro[5.5]undecane and its antipode, the minor component of the olive fruit fly pheromone
✍ Scribed by Yūsuke Yokoyama; Hirosato Takikawa; Kenji Mori
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 323 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0968-0896
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📜 SIMILAR VOLUMES
An acid-catalysed rearrangement of the THP-ether of homoallylic alcohol gives ready access to an O-protected derivative of 4-hydroxytetrahydropyran and thence by two further steps to provide a short and highly stereoselective route to the title spiroketal.
Application of a novel double intramolecular hetero-Michael addition (DIHMA) strategy to spiroketal synthesis was illustrated by a concise synthesis of (±)-(4S\*,6S\*)-4-hydroxy-1,7-dioxaspiro[5.5]undecane, a Dacus oleae olive fly pheromone.
## Abstract (4__R__,5__R__,6__S__,7__E__,9__E__)‐4,6,8‐Trimethyl‐7,9‐undecadien‐5‐ol (1) and its antipode 1′, the female specific compound of the woodroach __Cryptocercus punctulatus__, were synthesized by starting from methyl (__R__)‐3‐hydroxy‐2‐methylpropanoate (C).