Enantiospecific total synthesis and absolute configurational assignment of (-)-punctatin A (antibiotic M95464)

LA Paquette, T Sugimura

Index: Paquette, Leo A.; Sugimura, Takashi Journal of the American Chemical Society, 1986 ,  vol. 108,  # 13  p. 3841 - 3842

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Citation Number: 44

Abstract

(+)-Diketone 2, readily available in an enantiomeric purity of 99.6%: underwent regie and stereocontrolled hydride reduction'together with conversion* to SEM ether 3 in 88% yield (Scheme I). Alkylation of the thermodynamic enolate of 39 with 1-iodo-2-methylpropane provided 4 (54%) with the intention that the alkyl side chain ultimately become the carbocyclic backbone of the four-membered ring. As expected, I0 4 was reduced by ...