207302-95-2Relevant academic research and scientific papers
Synthetic studies of antitumor macrolide rhizoxin: Stereoselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits
Burke, Steven D.,Hong, Jian,Lennox, Joseph R.,Mongin, Andrew P.
, p. 6952 - 6967 (1998)
A triply convergent synthetic approach which culminates in the enantioselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin is described. The central C(12)-C(20) subunit 4 has been prepared efficiently via diastereoselective enzymatic acetate hydrolysis of 15 with porcine pancreatic lipase, a chelation- controlled Ireland-Claisen rearrangement (10 → 12) combined with kinetic bromolactonization (12 → 14), and Mitsunobu inversion (23 → 26) to introduce the three contiguous C(15)-C(17) stereocenters. Formation of the C(18)-C(19) trisubstituted (E)-olefin was achieved by a stereoselective Horner-Wadsworth-Emmons reaction. The central segment 4 and the oxazole chromophore side chain 3 were coupled using another highly stereoselective Horner-Wadsworth-Emmons reaction. Two different lactone subunits [C(1)-C(9) segment 5 and C(3)-C(10) segment 47] were also prepared, employing a thermodynamically controlled diastereotopic group differentiation tactic for establishing the C(5) stereochemistry.
Stereoselective syntheses of the rhizoxin C(1)-C(9) and C(12)-C(26) subunits
Burke, Steven D.,Hong, Jian,Mongin, Andrew P.
, p. 2239 - 2242 (2007/10/03)
Stereoselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin are described. Chelation-controlled Ireland-Claisen rearrangement, stereoselective Horner-Wadsworth-Emmons reactions and a thermodynamically-cont
