Tetrahedron Letters

Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno …

S Halila, M Benazza, G Demailly

Index: Halila, Sami; Benazza, Mohammed; Demailly, Gilles Tetrahedron Letters, 2001 , vol. 42, # 19 p. 3307 - 3310

Full Text: HTML

Citation Number: 25

Abstract

Polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane rings have been readily obtained in excellent yields (78–95%) from thioheterocyclisation of the bielectrophilic peracetylated α, ω-dibrominated derivatives of tetritols (erythritol (1) and d, l-threitol (4)), pentitols (xylitol (7), ribitol (10) and d-arabinitol (14)) and hexitols (d-mannitol (17) and d- glucitol (20)), respectively. With 2, 3, 4, 5-tetra-O-acetyl-1, 6-dibromo-1, 6-dideoxy-d- ...