213692-58-1Relevant articles and documents
Synthetic studies on the starfish alkaloid imbricatine. A chiral synthesis of tri-O-methylimbricatine
Ohba, Masashi,Nishimura, Yoshikazu,Kato, Miyako,Fujii, Tozo
, p. 4999 - 5016 (2007/10/03)
A detailed account is given of the chiral synthesis of tri-O- methylimbricatine (3), the triO-methyl derivative of the structurally unique benzyltetrahydroisoquinoline alkaloid imbricatine (2) isolated from the starfish Dermasterias imbricata. The route begins with the asymmetric synthesis of the sulfur-containing D-phenylalanine derivative (R)-11a and includes its conversion into the cis-benzyltetrahydroisoquinoline moiety 26a possessing the thiol group and construction of the 5-arylthio-3-methyl-L- histidine portion. The correctness of the structure and absolute configuration proposed for imbricatine has been unequivocally confirmed as a result of the present synthesis.