Total synthesis of (18S)- and (18R)-homolargazole by rhodium-catalyzed hydrocarboxylation.
Homolargazole derivatives, in which the macrocycle of natural largazole is extended by one methylene group, were prepared by the recently developed rhodium-catalyzed hydrocarboxylation reaction onto allenes. This strategy gives access to both the (18S)- and (18R)-stereoisomers in high stereoselectivity under ligand control.
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Bg. (Germany), Fax: (+49) 761-203-8715.
Christoph
C
Schotes
Dmytro
D
Ostrovskyi
Johanna
J
Senger
Karin
K
Schmidtkunz
Manfred
M
Jung
Bernhard
B
Breit
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000466:Alkadienes; D047630:Depsipeptides; D008024:Ligands; D013844:Thiazoles; C527895:largazole; C025947:propadiene; D012238:Rhodium
macrocyclic compounds; medicinal chemistry; rhodium; stereoselective catalysis; synthetic drugs