Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).
The ZACA reaction has been shown to proceed satisfactorily with internally OH-substituted 1-alkenes, provided that the OH group is unprotected and non-allylic. This reaction was used for reagent-controlled asymmetric construction of 3. Allylic alcohol was converted to 2 in seven steps via iterative ZACA processes and simple chromatography. (-)-Spongidepsin (1) was synthesized by using 2 and 3 through application of the esterification-amidation-ring-closing metathesis protocol previously reported.
Zhu
Gangguo
G
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Negishi
Ei-ichi
E
D000475:Alkenes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D047630:Depsipeptides / Q000138:chemical synthesis*; D015040:Zirconium / Q000737:chemistry*
D000475:Alkenes; D047630:Depsipeptides; C498389:spongidepsin; D015040:Zirconium; D000535:Aluminum