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Synlett 1998; 1998(7): 735-736
DOI: 10.1055/s-1998-1778
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A New Stereoselective Route to (-)-Octalactin A Based on Intramolecular SmI2 Promoted Reformatsky Reaction

Susumu Inoue* , Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama
  • *Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8131, Japan; Fax 81-95-8 48-42 86
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Publication Date:
31 December 2000 (online)

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A novel stereoselective synthesis of the key left-hand fragment of (-)-octalactin A has been achieved from methyl (R)-3-hydroxy-2-methylpropionate employing SmI2 promoted intramolecular Reformatsky reaction of a δ-(bromoacetoxy)aldehyde as a key step.

octalactin - enantioselective synthesis - eight-membered lactone - samarium(II) iodide - intramolecular Reformatsky reaction