Total synthesis of coraxeniolide-A.
The first total synthesis of optically active coraxeniolide-A (1a) and 4-epi-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniolide family. The use of the Grob-fragmentation was pivotal for the stereospecific elaboration of the nine-membered ring. Coraxeniolide-A (1a) was synthesized in 28 steps by using the Hajos-Parrish diketone 2 as starting material which is available enantiomerically pure.
Renneberg
D
D
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Pfander
H
H
Leumann
C J
CJ
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003063:Cnidaria / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D011714:Pyrans; C420544:coraxeniolide A