Tetrahedron p. 2885 - 2914 (1993)
Update date:2022-08-03
Topics:
Dormoy, Jean-Robert
Heymes, Alain
Total synthesis of modified ellipticines 1c and 1f is described from 2-chloronicotinic acid and respectively 5-methoxy -indole and 5-azaindole in 11 to 13 steps with overall yields of 11% and 18%. A new route to 5-azaindole has also been developed. The synthetic strategy calls for frequent use of homo- and hetero aromatic metallation reactions necessiting resolution of problems associated with the presence of the pyridine ring. With respect to the numerous synthesis described in the litterature, the originality of this approach resides above all in the formation of ring C in basic medium.1 such conditions being dictated by the presence of the pyridine A ring in the case of 1f. Both synthesis have been extrapolated to produce several kilogrammes of final product. That first part deals with the preparation of the precursors.
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Doi:10.1002/ardp.19933260208
(1993)Doi:10.1016/0008-6215(93)84195-C
(1993)Doi:10.1007/BF03020385
(1939)Doi:10.1021/jo01266a046
(1968)Doi:10.1016/0022-1902(67)80153-2
(1967)Doi:10.1177/147323000303100310
(1898)
