Biosynthesis. Part 30. 1 Colchicine: studies on the ring expansion step focusing on the fate of the hydrogens at C-4 of autumnaline

PW Sheldrake, KE Suckling, RN Woodhouse…

Index: Sheldrake, Peter W.; Suckling, Keith E.; Woodhouse, Robert N.; Murtagh, Amanda J.; Herbert, Richard B.; Barker, Alan C.; Staunton, James; Battersby, Alan R. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 18 p. 3003 - 3009

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Citation Number: 24

Abstract

Autumnaline 1 is a key biosynthetic precursor of colchicine 4. Syntheses are described of autumnalines that are labelled stereospecifically with tritium at C-4 of their isoquinoline ring. This corresponds to C-12 of the later intermediate dienone 2. Incorporation experiments with the labelled autumnalines using Colchicum autumnale plants show that (a) both HR and HS at C-4 of 1 are fully retained as the dienone is generated,(b) there is stereospecific loss of ...