Synthesis and reactivity of endocyclic α,β-epoxy-γ-butyrolactones

✍ Scribed by Robert K. Boeckman Jr; Edward W. Thomas

• Book ID: 104225365
• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 274 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92571-1

✦ Synopsis

h the course of our studies toward the total synthesis of the fungal metabolite Cerulenin ($1 we required 01, ,%epoxy 7' lactone (2) as a key intermediate. __ A review of the literature revealed that endocyclic Cr, fl-epoxylactones such as 2 had not been prepared previously. This class of substances could have quite interesting biological activity in their own right, since these substances could function as bifunctional alkylating-acylating agents bycleavage of both the lactone and epoxide by nucleophiles. This possibility would permit them to act as cross linking agents in biological systems, 2 Consequently, we set out to develop a general method for the preparation of m, pepoxy-y-lac-