Tetrahedron

Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)-butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron

S Hanessian, T Abad-Grillo, G McNaughton-Smith

Index: Hanessian, Stephen; Abad-Grillo, Teresa; McNaughton-Smith, Grant Tetrahedron, 1997 ,  vol. 53,  # 18  p. 6281 - 6294

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Citation Number: 18

Abstract

Studies to try and epimerize the C-2 centre in compound 5 using a variety of bases proved challenging. Only tert-butoxide/THF gave a reasonable ratio (2:5 = 1:1), while other bases including DBU, failed to generate any of the desired isomer. Formation of the lithium enolate (dianion) of 6 followed by protonation with a variety of compounds bearing acidic protons on either oxygen or carbon were unrewarding. ... Encouragingly, the amount of C-2 epimer 13 was found ...