Tetrahedron letters

Singlet oxygen in synthesis. Oxazoles as carbonyl 1, 1-dipole synthons.

HH Wasserman, RW DeSimone, WB Ho, KE McCarthy…

文献索引：Wasserman; DeSimone; Ho; McCarthy; Spencer Prowse; Spada Tetrahedron Letters, 1992 , vol. 33, # 47 p. 7207 - 7210

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被引用次数: 16

摘要

Abstract 2, 5-Diphenyloxazole has been utilized in a two-step sequence as a carbonyl 1, 1- dipole synthon as illustrated by the synthesis of 7-heptanolide, α-benzyloxy δ-valerolactone, and 9-nonanolide. Alkylation of 4-lithio-2, 5-diphenyloxazole, followed by singlet oxygen oxidation yields a triamide which undergoes cyclization to the lactone.