From a biogenetic scenario to a synthesis of the ABC ring of manzamine A.
On the basis of a biogenetic proposal for explaining the biogenesis of manzamine A, the cycloaddition of dihydropyridinium salt 26 with diene derivative 5 leads to adducts 27. These adducts, as well as their related and previously described analogues 9, are now shown to be precursors of diene derivatives such as 10, 13, and 28. Treatment of diene 32 with sodium azide resulted in a one-step formation of the tricyclic imino derivative 34. This key intermediate was further transformed into tricyclic derivative 40, which possesses the essential features of the ABC ring of manzamine A.
Herdemann
Matthias
M
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Al-Mourabit
Ali
A
Martin
Marie-Thérèse
MT
Marazano
Christian
C
D000818:Animals; D001711:Biotransformation; D002227:Carbazoles; D002384:Catalysis; D002855:Chromatography, Thin Layer; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship
D002227:Carbazoles; D007211:Indoles; D011758:Pyrroles; C078290:manzamine A