Synthesis of the antiproliferative agent hippuristanol and its analogues via Suárez cyclizations and Hg(II)-catalyzed spiroketalizations.
A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereoselection was obtained throughout the construction of the key spiroketal unit. Suárez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.
Département de Chimie, Université de Sherbrooke, Sherbrooke, QC, Canada, J1K 2R1.
Kontham
K
Ravindar
Maddi Sridhar
MS
Reddy
Lisa
L
Lindqvist
Jerry
J
Pelletier
Pierre
P
Deslongchamps
D000818:Animals; D002384:Catalysis; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D008628:Mercury / Q000737:chemistry*; D008968:Molecular Conformation; D011817:Rabbits; D012156:Reticulocytes / Q000166:cytology* / Q000187:drug effects*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013261:Sterols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D005663:Furans; D013141:Spiro Compounds; D013261:Sterols; C510125:hippuristanol; C520774:spiroketal; D008628:Mercury