Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence.
The synthesis of the tricyclic enone 2, corresponding to the AB subunit of the novel tyrosine kinase inhibitor angelmicin B, is described. The strategy centers on an intramolecular Diels-Alder (IMDA) reaction on triene 4 to provide the complex decalin 3, which is elaborated to 2. Other key steps are the formation of the THF ring in 2 through a tandem alkoxy radical fragmentation-etherification on the lactol derived from 3, and the synthesis of 4 via a ring-closing ene-yne metathesis (RCEYM).
Li
Jialiang
J
Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, USA.
Todaro
Louis J
LJ
Mootoo
David R
DR
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D015394:Molecular Structure; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*
D000880:Anthraquinones; C083655:angelmicin B; D011505:Protein-Tyrosine Kinases