Synthesis of the ring system of phomactin D using a Suzuki macrocyclization.
[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.
Kallan
N C
NC
Department of Chemistry and Biochemistry, University of Colorado, Boulder 80309-0215, USA.
Halcomb
R L
RL
D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D010972:Platelet Activating Factor; C103093:phomactin D