Tetrahedron

Asymmetric synthesis of (2R)-and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism

C Jacoby, JC Braekman, D Daloze

Index: Jacoby, Claude; Braekman, Jean-Claude; Daloze, Desire Tetrahedron, 1996 , vol. 52, # 31 p. 10473 - 10484

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Citation Number: 6

Abstract

(2R)-(+)-and (2S)-(−)-2-iodohexadecanal 1 with ee's≥ 89% were synthesized in five steps and 62% overall yield from chiral enol ethers Z-and/or E-7, via the iodocyclization with IC1 and chromatographic separation of the resulting diastereomeric 1′-iododioxanes 8. The ee's of (2S)-and (2R)-1 have been determined after their transformation to the (R)-O- methylmandelate esters 11 and 12 or to the epoxides (2R)-and (2S)-13, respectively. ...