Tetrahedron p. 6447 - 6458 (1986)
Update date:2022-07-29
Topics:
Mori, Atsunori
Arai, Isao
Yamamoto, Hisashi
Nakai, Hisao
Arai, Yoshinobu
Asymmetric Simmons-Smith reactions of α,β-unsaturated acetals derived from chiral dialkyl tartrate or (2R,4R)-2,4-pentanediol are described.Treatment of the acetal with diethylzinc and methylene iodide gives a cyclopropane with high diastereoselectivity.The acetal group is readily transformed to the aldehyde or the ester group.In addition, the method is successfully applied to the enantioselective synthesis of 5,6-methanoleukotriene A4, a stable and selective inhibitor of leukotriene biosynthesis.
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