The preparation of the first α-vinylidenepenams

✍ Scribed by John D. Buynak; H.B. Borate; Chad Husting; Trace Hurd; Jyoti Vallabh; Jacob Matthew; Jarvis Lambert; Upali Siriwardane

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 196 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)80677-2

✦ Synopsis

Benzyl esters of the first 6-vinylidenepenams have been prepared by reaction of 6-position propargylic triflates with higher order organocuprates.

This methodology permits a great deal of versatility in the introduction of substituents at the terminal allenyl position.

Our interest in allene chemistry, p-lactams, and strained organic molecules recently led us to prepare the first f3-lactam with a fused allene alpha to the carbonyl. 1 However, these primarily monocyclic p-lactams did not possess the relatively strained, highly functional, bicyclic skeletons common to many of the biologically active molecules (ex. penams, penems, cephams, carbapenems, etc.). The bicyclic p-lactam antibiotics continue to interest the biochemical and medicinal community.

Recently, for example, Merck workers demonstrated that