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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
Author(s) -
Giersch Wolfgang,
SchulteElte Karl H.
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730322
Subject(s) - chemistry , ozonolysis , ene reaction , enantiomer , natural product , diol , stereochemistry , yield (engineering) , octene , organic chemistry , catalysis , materials science , ethylene , metallurgy
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.