A hetero-Diels-Alder approach to complex pyrones: an improved synthesis of the spongistatin AB spiroketal.
The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Michael T
MT
Crimmins
Aaron C
AC
Smith
D000818:Animals; D000970:Antineoplastic Agents; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000970:Antineoplastic Agents; D018942:Macrolides; D011753:Pyrones; C083856:spongistatin 1; D000095702:Polyether Toxins