Tetrahedron p. 2479 - 2482 (1985)
Update date:2022-07-31
Topics:
Suresh, R. V.
Iyer, C. S. Rukmani
Iyer, P. R.
Erythrinin A (10) has been synthesised by the oxidative rearrangement of dihydropyranochalcone 1 with thallium(III)nitrate (TTN) in trimethyl orthoformate (TMOF) to the dimethyl acetal 2, followed by cyclisation to 3, demethylation to 6 and dehydrogenation.Compound 10 could also be obtained from chalcone 4 on similar rearrangement followed by cyclisation, demethoxymethylation and dehydrogenation.In another route, chalcone 7 was oxidatively rearranged with TTN in TMOF, to 8 which on treatment with HCl yielded 10.
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Doi:10.1271/bbb.90047
(2009)Doi:10.1039/C8DT03210F
(2018)Doi:10.1016/0040-4039(94)88070-0
(1994)Doi:10.1021/jm00150a008
(1985)Doi:10.1021/ja01520a047
(1959)Doi:10.1021/jo01024a508
(1964)
