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

Full Text: HTML

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. ...

Related Articles:

Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides

[Lafont, Dominique; Bouchu, Marie-Noelle; Girard-Egrot, Agnes; Boullanger, Paul Carbohydrate Research, 2001 , vol. 336, # 3 p. 181 - 194]

Asymmetric synthesis of (+)-passifloricin A and its 6-epimer

[Chandrasekhar; Rambabu; Reddy, A. Syamprasad Tetrahedron Letters, 2008 , vol. 49, # 29-30 p. 4476 - 4478]

A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen (Co) III (OAc) catalysts

[Savle, Prashant S.; Lamoreaux, Marika J.; Berry, John F.; Gandour, Richard D. Tetrahedron Asymmetry, 1998 , vol. 9, # 11 p. 1843 - 1846]

More Articles...