- Bharatamine A Novel Protoberberine Alkaloid of Aberrant Biogenetic Origin from Alangium lamarckii Thw.
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The structure elucidation and the synthesis of bharatamine, a biogenetic marvel being a protoberberine alkaloid unoxygenated in ring D, and its regioisomer isobharatamine have been discussed in detail.
- Pakrashi, S. C.,Mukhopadhyay, Ranjan,Dastidar, P. P. Ghosh,Bhattacharjya, Anup,Ali, E.
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p. 1003 - 1007
(2007/10/02)
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- A Convenient Total Synthesis of (+/-)-Bharatamine and (+/-)-Isobharatamine
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N,N-Dimethylbenzylamine (1) on lithiation with n-butyllithium followed by reaction with paraformaldehyde gives the 2-hydroxymethyl derivative (2). 2 on successive reactions with ClCOOEt, KCN and alc.KOH followed by cyclisation furnishes isochroman-3-one (3).Condensation of 3 with phenylethylamines (4a) and (4b), followed by cyclisation (PCl5), reduction (NaBH4), and debenzylation (EtOH-HCl) gives (+/-)-bharatamine (6c) and (+/-)-3-hydroxy-4-methoxy-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (isobharatamine, 6d), respectively in high yields.
- Patil, Sharadbala D.,Mali, R. S.
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p. 360 - 362
(2007/10/02)
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