Inventors:
Samuel Danishefsky - Englewood NJ, US
Vladimir Birman - New York NY, US
International Classification:
A61K031/497
A61K031/4439
A61K031/4433
A61K031/407
A61K031/365
C07D491/02
US Classification:
514/410000, 514/468000, 548/421000, 549/298000, 514/255050, 514/338000, 544/405000, 546/276700, 546/284100
Abstract:
This invention provides a total synthesis of Merrillactone and Merrilactone analogues having the structure wherein Z is O or N—X, where X is H, straight or branched substituted or unsubstituted alkyl, alkenyl or alkynyl, or acyl, carbamoyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, aralkyl, amino, alkyl amino, or dialkyl amino; wherein each of Rand Ris H or Rand Rtogether are O; wherein each of Rand Ris H or Rand Rtogether are O; wherein each of Rand Ris, independently, H, alkyl, aralkyl, or aryl; wherein each of Rand Ris, independently, H or OR, where Ris alkyl or —C(O)—R, where Ris H, —CHR, —CHRR, —CRRR, —OR, alkenyl or alkynyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, aralkyl, amino, alkyl amino, or dialkyl amino, wherein each Ris straight or branched, substituted or unsubstituted alkyl, alkenyl or alkynyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, aralkyl, or amino; and wherein Ris straight or branched, unsubstituted alkyl, alkenyl or alkynyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, aralkyl, or amino, or wherein Rand Rtogether are O; wherein each of Rand Ris, independently, H, alkyl, OH, or OR, where Ris an alkyl, an acyl, or an amide, or Rand Rtogether are CH, or wherein Rand Rtogether are O; wherein if one of Ror Rand one of Ror Ris absent, a double bond is formed as indicated by the broken line; and wherein each of Rand Ris, independently, H, OH, or OR, where Ris an alkyl, an acyl, or an amide, or Rand Rtogether are O, or wherein Rand Rtogether are O, including intermediates in the synthesis.