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. DANIELI
Secondo
;
G. LESMA
Penultimo
;
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.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/183704
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 14
social impact