Enantioselective synthesis of a 3'-dephenylcryptophycin synthon.
An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert-butyldimethylsilyloxy-6-methyl-2,7-octadieno ate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and Cl' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.
Eggen
M J
MJ
Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA.
Georg
G I
GI
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D047630:Depsipeptides; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C096566:arenastatin A; C088419:cryptophycin