Modular synthesis of the C9-C27 degradation product of aflastatin A via alkyne-epoxide cross-couplings.
A modular approach to the synthesis of complex polyketide natural products is demonstrated for the synthesis of the C9-C27 degradation product from aflastatin A. The product of the cross-coupling of C23-C27 terminal alkyne with C17-C22 epoxide underwent functionalization of the resulting internal alkyne, which was then coupled similarly with C9-C16 epoxide. This synthesis concluded with regio- and stereoselective addition of methyl onto the internal alkyne followed by stereoselective hydroboration-oxidation.
Robles
Omar
O
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
McDonald
Frank E
FE
D000480:Alkynes / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000480:Alkynes; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D011760:Pyrrolidinones; C105377:aflastatin A