Total syntheses of macrocyclic marine alkaloids, haliclamines A and B: A convenient and expeditious assembly of 3-substituted pyridine derivatives with different alkyl chains to the bispyridinium macrocycle
The total syntheses of haliclamines A (1) and B (2), macrocyclic marine alkaloids closely related to the key bisdihydropyridine intermediate 3 of the biogenetically unique manzamine family, have efficiently been achieved via stepwise controlled inter- and intramolecular N-alkylations of 3- alkylpyridine derivatives such as 40 and 41. The general synthetic methodology toward the bispyridinium macrocycle 44, a key biogenetic equivalent of the polycyclic marine alkaloids, has been proposed through the total syntheses.
Total synthesis of haliclamine A, a macrocyclic marine alkaloid related to the key biogenetic intermediate of manzamines
The first total synthesis of haliclamine A (1), a macrocyclic marine alkaloid closely related to the key bisdihydropyridine intermediate 3 of the biogenetically unique manzamine family, has been efficiently achieved via stepwise inter- and intramolecular N-alkylations of 3-alkylpyridine derivatives 26 and 28.
Morimoto, Yoshiki,Yokoe, Chiho
p. 8981 - 8984
(2007/10/03)
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