✦ LIBER ✦
Enantiomeric 3,7-Dimethylocta-1,7-dienes as Useful Chiral Building Blocks. A New Access to Both Optical Antipodes of Natural (E)-3,7-Dimethyloct-2-ene-1,8-diol and (E)-3,7-Dimethyloct-2-ene-1,8-dicarboxylic Acid
✍ Scribed by Wolfgang Giersch; Karl H. Schulte-Elte
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- German
- Weight
- 371 KB
- Volume
- 73
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Ozonolysis of the easily available monoterpenoids (−)‐1 and (+)‐1 leads in high yield to the ketoaldehydes (−)‐4 and (+)‐4, which serve as convenient intermediates for efficient new routes to both optical antipodes of the naturally occurring octenediol (E)‐2 (Monarch butterfly secretion product) and octene‐dicarboxylic acid (E)‐3 (Callosobruchus chinensis sex pheromone). All steps proceed with almost complete retention of configuration, ensuring the synthesis of the target compounds with high optical purity.