Total synthesis of the proposed structure of briarellin J.

ABSTRACT: The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

SUBMITTER: Crimmins MT 

PROVIDER: S-EPMC2966518 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature