Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.

ABSTRACT: We report an approach to the core of the manzamine alkaloid keramaphidin B that relies on the strain-promoted cycloaddition of an azacyclic allene with a pyrone trapping partner. The cycloaddition is tolerant of nitrile and primary amide functional groups and can be complemented with a subsequent retro-Diels-Alder step. These efforts demonstrate that strained cyclic allenes can be used to build significant structural complexity and should encourage further studies of these fleeting intermediates.

SUBMITTER: Mehta MM 

PROVIDER: S-EPMC10460088 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature