Synthesis of 6,6'-binaphthopyran-2-one natural products: pigmentosin A, talaroderxines A and B.
Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Charles I
CI
Grove
Michael J
MJ
Di Maso
Firoz A
FA
Jaipuri
Michelle B
MB
Kim
Jared T
JT
Shaw
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008011:Lichens / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D009281:Naphthalenes; D011753:Pyrones; C579016:pigmentosin A; C579018:talaroderxine A; C579017:talaroderxine B