Synthesis of an advanced intermediate for (+)-pillaromycinone. Staunton-Weinreb annulation revisited.
Condensation of an orsellinate anion with a 2-cyclohexenone (Staunton-Weinreb annulation) afforded a linear tetracycle which was converted to a protected derivative of 12a-epipillaromycinone. Methodology for introducing a 12a-hydroxyl substituent into the tetracycle with correct (R) configuration is described.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA. james.white@oregonstate.edu
Demnitz
F W J
FW
Xu
Qing
Q
Martin
William H C
WH
D018943:Anthracyclines / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry
D018943:Anthracyclines; D009930:Organic Chemicals; C531275:pillaromycinone