Helvetica Chimica Acta p. 856 - 875 (1997)
Update date:2022-08-05
Topics:
Brienne, Marie-Josephe
Gabard, Jacqueline
Leclercq, Martine
Lehn, Jean-Marie
Cheve, Michel
The chiral biyclic bis-lactams of structures 3 and 4 were synthesized from the key intermediate 2′b, the N,N′-bis(4-methoxybenzyl) derivative of 2 (X = MeO) (Scheme 6). The synthesis of this intermediate involved two key steps: 1) a double condensation of glyoxylic acid/anisamide (= oxoacetic acid/4-methoxybenzamide) adduct 11c with veratrole (1,2-dimethoxybenzene; 10) allowed the introduction of two glycine units at the 4,5-positions of the veratrole ring to give 18c (Schemes 3 and 4); 2) in order to circumvent the hydrolysis of 4-methoxybenzoyl protective groups which proved to be unfeasible, these groups were transformed into 4-methoxybenzyl groups through a sequence involving thiocarbonylation followed by reduction (Scheme 5). Thereafter, the double intramolecular cyclization of the resulting diamino diester 22c proceeded easily to afford 2′b. This intermediate may be transformed via the tetrol 2′g or the diol 2′h into the N-protected derivatives of 2 (X = OR) and of 3 (X = OCOR). Cleavage of the 4-alkoxybenzyl groups was achieved by ceric ammonium nitrate. However, when the aromatic ring bore ether functions (N-protected 2), this normal reaction was accompanied by the oxidative ring cleavage to give the diene-diester structure 4 (Schemes 5 and 6).
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Doi:10.1021/jo9701445
(1997)Doi:10.1016/0022-328X(86)84029-3
(1986)Doi:10.1016/S0040-4039(97)00934-9
(1997)Doi:10.1016/S0960-894X(97)00228-X
(1997)Doi:10.1016/j.bmc.2004.02.025
(2004)Doi:10.1002/oms.1210140503
(1979)