Two alternative routes have been developed for the synthesis of trichotomine dimethyl ester 2. Both routes involve the synthesis of keto lactam 3 by reaction of the chiral imine 4 [obtained starting from (S)-(-)-tryptophan] with oxalyl chloride. The elaboration of 3 into 2 is achieved through the intermediacy of diazo lactam 5 and subsequent copper-assisted thermolysis furnishes 2. A more efficient route involves a carbene-mediated olefination of keto lactam 3 to give trichotomine dimethyl ester 2 in good yield. The preparation of decarboxytrichotomine 6 is also described.
BIS(INDOLE) ALKALOIDS - A NONBIOMIMETIC APPROACH TO THE BLUE PIGMENT TRICHOTOMINE DIMETHYL ESTER / G. PALMISANO, B. DANIELI, G. LESMA, R. RIVA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 50:18(1985), pp. 3322-3325.
BIS(INDOLE) ALKALOIDS - A NONBIOMIMETIC APPROACH TO THE BLUE PIGMENT TRICHOTOMINE DIMETHYL ESTER
B. DANIELISecondo
;G. LESMAPenultimo
;
1985
Abstract
Two alternative routes have been developed for the synthesis of trichotomine dimethyl ester 2. Both routes involve the synthesis of keto lactam 3 by reaction of the chiral imine 4 [obtained starting from (S)-(-)-tryptophan] with oxalyl chloride. The elaboration of 3 into 2 is achieved through the intermediacy of diazo lactam 5 and subsequent copper-assisted thermolysis furnishes 2. A more efficient route involves a carbene-mediated olefination of keto lactam 3 to give trichotomine dimethyl ester 2 in good yield. The preparation of decarboxytrichotomine 6 is also described.Pubblicazioni consigliate
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