Abstract
Ethyl-2,3-dihydro-1-phenyl-1H-pyrrolizine 19 and 1-(2-aminophenyl)-6-ethyl-2,3-dihydro- 1H-pyrrolizine 30 were synthesized starting from the pyrroles 4-acetylpyrrol-2-yl phenyl ketone 13 and 4-acetylpyrrol-2-yl 2-(dimethylaminomethylenamino)phenyl ketone 26, respectively, using vinyltriphenylphosphonium bromide in an intramolecular Wittig reaction for the formation of the second five-membered ring.
Highlights
The variety of indole alkaloid skeleta,1of greater or lesser complexity, has been a frequently employed proving ground for novel synthetic methodologies and strategies
One of the few groups of monoterpenoid indole alkaloids which has not yet been the subject of a successful total synthesis, is the group characterised by the presence of a C-7–C-16 bond4 – akuammiline 1 represents this structural type in its simplest form
Our personal interest in this group of alkaloids traces back to that period when the Manchester Chemistry Department was priviliged to number amongst its academic staff Arthur Birch and Rod Rickards, and one of the present authors studied Akuamma alkaloids for PhD.[6]
Summary
The variety of indole alkaloid skeleta,1of greater or lesser complexity, has been a frequently employed proving ground for novel synthetic methodologies and strategies. One of the few groups of monoterpenoid indole alkaloids which has not yet been the subject of a successful total synthesis, is the group characterised by the presence of a C-7–C-16 bond4 – akuammiline 1 represents this structural type in its simplest form. Our personal interest in this group of alkaloids traces back to that period when the Manchester Chemistry Department was priviliged to number amongst its academic staff Arthur Birch and Rod Rickards, and one of the present authors studied Akuamma alkaloids for PhD.[6] It is a pleasure to contribute this paper for the issue of Arkivoc which commemorates Professor. Rickards' 70th Birthday, in recognition of his contributions to natural product chemistry in Manchester, and subsequently in Canberra, and of his friendship and encouragement as a colleague in Manchester
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