Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser-Kraus Annulation
A stereoselective synthesis of a pyranonaphthoquinone derivative found in aromatic polyketide-derived aphid pigments is reported herein. This approach features the anionic [4+2]-annulation of phthalides with a carbohydrate-derived optically active enone.
Synthesis of a tetrasubstituted arylphosphonate via the anionic phospho-Fries rearrangement
The anionic phospho-Fries rearrangement of phosphoric acid (3,5-di-isopropoxy)phenyl ester diethyl ester (11) gave rise to (2-hydroxy-4,6-di-isopropoxy-phenyl)phosphonic acid diethyl ester (12) in excellent yield. The phenol functionality of 12 was converted to the corresponding triflate which was coupled with vinyltributylstannane, under Stille conditions, to give a styrene. This molecule is intended to serve as the aromatic fragment in the synthesis of a phosphorus-based transition-state analogue for the hydrolysis of the S-(-)-zearalenone lactone.
Jayasundera, Krishanthi P.,Watson, Amy J.,Taylor, Carol M.
p. 4311 - 4313
(2007/10/03)
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