Hasubanonine, biosynthesis

Protostephanine and Hasubanonine.—The unravelling of the biosynthesis of pro-tostephanine (36) and hasubanonine (37), both produced by Stephania japonica,... 

Hasubanonine, Protostephanine, and Laurifinine. — Full papers on the biosynthesis of hasubanonine (31) and protostephanine (32), which are most interesting benzylisoquinoline variants, have been published an epic piece of research. (Preliminary accounts ... 

Fig. 32.19. Proposed biosynthesis of hasubanonine (Battersby et al., 1981c used with permission of the copyright owner. The Royal Society of Chemistry, Cambridge).

Battersby, A. R., R. C. F. Jones, R. Kazlauskas, C. W. Thornber, S. Ruchirawat, and J. Staunton, Biosynthesis, Part 24. Speculative incorporation experiments with 1-benzyli-soquinolines and a logical approach via C6-C2 and C -Cj precursors to the biosynthesis of hasubanonine and protostephanine, J. Chem. Soc. Perkin Trans. I, 2016-2029 (1981a). 

Battersby AR, Staunton J, Summers MC, Southgate R (1979) Studies of enzyme-mediated reactions, part 9. Stereochemistry of oxidative ring cleavage adjacent to nitrogen during the biosynthesis of chehdonine. J Chem Soc Perkin Trans 1 45-52 Battersby AR, Jones RCF, Minta A, Ottridge AP, Staunton J (1981) Biosynthesis, part 25. Proof that hasubanonine and protostephanine are biosynthesised from the 1-benzylisoquinoline system. J Chem Soc Perkin Trans 1 2030-2039... 

Scheme 15. Biosynthesis of hasubanonine by in vivo experiments with S. japonica (a) 59) and mechanistic considerations (b) 61).

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