Ancistrocladidine

Two naphthalene-isoquinoline groups of alkaloids, ancistrocladidine (53) and ancistrotectorine (54), were isolated from Ancistrocladus heyneanus Wall [295], and A. tectorius (Lour.) Merr [296], respectively. The members of the plant family, ancistrocladaceae, are distributed in tropical Asia and Western Africa. Some are regarded as traditionally medicinal plants. The root of A. tectorius has been used to treat dysentery and malaria [296],... 

Ancistrocladus tectorius (Lour.) Merr. (entire plant, leaves) Ancistrocladaceae Ancistrocladidine (43) Ancistrotectorine (38,44)... 

The first enantioselective total synthesis of the 7,3 -linked naphthylisoquinoline alkaloid (-)-ancistrocladidine was accomplished by J.C. Morris and co-workers. The key steps of the synthesis were the Pinhey-Barton ortho-arylation and the Bischier-Napieralski cyclization. The natural product was isolated from the 1 1 mixture of atropisomers by recrystallization from toluene/petroleum ether. 

Bungard, C. J., Morris, J. C. First Total Synthesis of the 7,3 -Linked Naphthylisoquinoline Alkaloid Ancistrocladidine. Org, Lett, 2002, 4, 631-633. 

Use of this method to form the extremely hindered biaryl linkage enabled completion of tlie first total synthesis of the rare 7,3 -linked naphthylisoquinoline alkaloid, ancistrocladidine (Scheme 13.21) [46]. 

A group of naphthylisoquinoline alkaloids has been identified of which twenty one have so far been isolated from Anois-trccladus and Tr-Lphyophyllwis pecies these being the 7-B-naphthylisoquinoline ancistrocladidine (10) and the 5 and 7 a-naphthyl-compounds listed in tables 4 and 5 respectively. 

Ancistrocladonine (14), Ancistroealaensine (15) Ancistrocladidine, Ancistrocladine (11), Ancistrocladinine (12), Ancistrocladisine... 

O-methylancistrocladine (5) (75) were also isolated by Govindachari and coworkers and structurally determined. Besides this 5-1 type, the 7-l -coupled alkaloid ancistrocladisine (18) (76), and the 7-2 product ancistrocladidine (21) (77) were also found in A. heyneams and were completely elucidated (18) with all their chiral centers. The quality and reliability of this work can be judged from the fact that the two latter structures 18 and 21 were, much later (79), confirmed by X-ray analysis. 

Among them, 10 of the alkaloids possess a junction between C-5 and C-1, and seven of the alkaloids possess a junction between C-7 and C-T. The last two alkaloids, ancistrocladidine and ancistrotectorine, possess a junction between C-7 and C-3 [2]. Ancistrotectorine was isolated from A. tectorius in 0.016% yield, and its chemical structure, including the absolute configuration, was reported [2]. 

Amphetamine, AS Amphotericins, Y26 Amurensine, K1 jS-amyrane, T42 Amyrins, T42 Anabasine, K18 Anaferine, K19 Anagyrine, K21 Anatabine, K18 Ancistrocladidine, K2 Ancistrocladinine, K2 Ancistrocladisine, K2 Ancistrocladine, K2 ... 

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