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Pheromone Syntheses, LXXVIII. Synthesis of the Four Thermodynamically Stable Stereoisomers of 2,7-Dimethyl-1,6-dioxaspiro[4.6]undecane, a Component of the Volatile Secretion from the Mandibular Glands ofAndrena haemorrhoa F.

✍ Scribed by Mori, Kenji ;Soga, Hiroshi ;Ikunaka, Masaya

Publisher: John Wiley and Sons
Year: 1985
Tongue: English
Weight: 683 KB
Volume: 1985
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198519851109

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✦ Synopsis

The title compounds (2R,5S,7R)-1, (2S,5S,7R)-l, (2R,5R,7S)-l, and (2S,5R,7S)-l were synthesized from ethyl (S)-lactate (3) and the (R)-or (S)-enantiomers of ethyl 3-hydroxybutanoate (4a). The formation of the spiro acetal 1 from 2b proceeds stereoselectively. Various spiro acetals with axial S-chirality at the spiro center were shown to be dextrorotatory at 589 nm.

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Pheromone Synthesis, LXIV. Synthesis of the Enantiomers of 2-Methyl-1,7-dioxaspiro[5.6]-dodecane, a Component of the Volatile Secretion from the Mandibular Glands ofAndrena haemorrhoa F.

✍ Mori, Kenji ;Katsurada, Manabu 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 English ⚖ 301 KB

## Abstract The syntheses of the title compounds (2__R__,6__S__)‐**1** and (2__S__,6__R__)‐**1** from (__R__)‐ and (S)‐β‐hydroxybutyrate **3** are described. The formation of the spiroacetal **1** from (__R__)‐**9** proceeded stereoselectively to give only (2__R__,6__S__)‐**1**. Similarly (__S__)‐*