Kallan N C, Halcomb R L
Department of Chemistry and Biochemistry, University of Colorado, Boulder 80309-0215, USA.
Org Lett. 2000 Aug 24;2(17):2687-90. doi: 10.1021/ol0062345.
[reaction: see text]The ring system of phomactin D was synthesized in racemic form in an efficient manner from 2,3-dimethylcyclohexanone. Notable transformations include (1) an alkylation of the enolate of a vinylogous thiolester to install a quaternary stereocenter, (2) a conjugate addition of cyanide to an alpha,beta-unsaturated aldehyde, (3) the formation of a Weinreb amide directly from a cyanohydrin, and (4) an intramolecular Pd-mediated Suzuki coupling of a B-alkyl-9-BBN derivative and a vinyl iodide to form the macrocyclic ring.
