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Synlett 1995; 1995(5): 407-408
DOI: 10.1055/s-1995-5001
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Enantioselective Synthesis of Macrolide Pheromones, (5Z, 13S)-5-Tetradecen-13-olide and (9R)-Decan-9-olide, by Using Mn-Salen Catalyzed Asymmetric Epoxidation as a Key Step

Tetsuya Hamada, Kazuhiro Daikai, Ryo Irie, Tsutomu Katsuki*
  • *Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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Highly enantioselective epoxidation of cis-enynes catalyzed by the newly developed Mn-salen catalyst 1 and subsequent LAH reduction provided optically active homopropargylic alcohols which served as useful building blocks for the synthesis of various pheromones. For example, (5Z, 13S)-5-tetradecen-13-olide and (9R)-decan-9-olide were synthesized from cis-enynes in a straightforward manner by using asymmetric epoxidation as a key step.

(salen)manganese(III) complex - asymmetric epoxidation - enyne - homopropargylic alcohol - macrolide pheromone