Stereocontrolled total synthesis of (.+-.)-pentenomycins. I-III, their epimers, and dehydropentenomycin I

…, SJ Branca, NN Pilla, MA Guaciaro

Index: Smith III; Branca; Pilla; Guaciaro Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1855 - 1869

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Citation Number: 108

Abstract

The total synthesis of (f)-pentenomycins 1-111 (la-c), their epimers (2a-c) termed by us epipentenomycins (I-111), and dehydropentenomycin I (3), seven members of the novel cyclopentanoid class of antibiotics, has been achieved. The synthetic routes are short (ca. five to seven steps), stereocontrolled, and for the most part highly efficient. Key elements of the strategies were (i) the development of a versatile a-ketovinyl anion equivalent which ...