Biosynthesis of the indolizidine alkaloid cyclizidine: incorporation of singly and doubly labelled precursors

FJ Leeper, SE Shaw, P Satish

Index: Leeper, Finian J.; Shaw, Susan E.; Satish, Padma Canadian Journal of Chemistry, 1994 , vol. 72, # 1 p. 131 - 141

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Citation Number: 14

Abstract

Incorporation of CH313C18O2Na and CD3CH213CO2Na into the indolizidine alkaloid cyclizidine 1, produced by Streptomyces species NCIB 11649, shows that the oxygen attached to C-2 is derived intact from acetate and that the cyclopropyl ring is derived from a single intact propionate unit. However, the level and stereochemistry of the incorporation of deuteriated sodium propionate indicates that it undergoes unexpected modification during ...