Asymmetric total synthesis of epolactaene. Part 1: Construction of epoxy-γ-lactam moiety and deduction of absolute stereochemistry

✍ Scribed by Shinji Marumoto; Hiroshi Kogen; Shunji Naruto

• Book ID: 104209438
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 997 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00367-1

✦ Synopsis

Enantioselective construction of the epoxy-T-lactam moiety of epolactaenc (1) was completed in 11 steps from (R)-lactaldehyde derivatives. Key steps include: (i) the stereoselective aldol reaction between (R)lactaldehyde and malonate ester; (ii) diastereospecific lactoniTation of malonate ester derivative 10; (iii) cyclization of 16 to epoxy-T-lactam derivative 2. Both enantiomers, (R,R)-2 and (S,S)-2, were synthesized, and their optical rotations were compared with that of (+)-epolactaene (1). The results suggest that the absolute configuration of 1 is (13R, 14R).