110117-69-6Relevant articles and documents
Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines
Ohba,Mukaihira,Fujii
, p. 1784 - 1790 (2007/10/02)
Chiral syntheses of 3-methyl-5-(phenylthio)-L-histidine (8a) and 3-methyl-5-(1-naphthalenylthio)-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involved were methylation of 9, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole (11), replacement of the 4-bromo group by an arylthio group in the aldehyde 14, and introduction of a chiral α-amino acid moiety into the chlorides 17a and 17b by the 'bis-lactim ether' method. The synthesis of the 4-(4-methoxybenzyl)thio analogue 17c, carried out in a similar manner, concluded formal syntheses of ovothiols A and C (1 and 3).
SYNTHESIS OF 5-ARYLTHIO-3-METHYL-L-HISTIDINE, A MODEL FOR THE STARFISH ALKALOID IMBRICATINE
Ohba, Masashi,Mukaihira, Takafumi,Fuji, Tozo
, p. 21 - 26 (2007/10/02)
Syntheses of 3 methyl-5-phenylthio-L-histidine (8a) and 3-methyl-5-(1-naphthyl)thio-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have now become feasible through a 10-step route starting from 4(5)-bromoimidazole (9).The key steps involve replacement of the 4-bromo group by an arylthio group in the aldehyde (14) and construction of the L-alanine moiety in the chlorides (17a,b) by the "bis-lactim ether" method.
Total Synthesis of Marine Mercaptohistidines: Ovothiols A, B, and C
Holler, Tod P.,Ruan, Fuqiang,Spaltenstein, Andreas,Hopkins, Paul B.
, p. 4570 - 4575 (2007/10/02)
Syntheses of ovothiols A and C in optically active form and ovothiols A and B in racemic form are reported.In all cases, synthesis of an S-protected mercaptoimidazole is followed by elaboration of an amino acid side chain.
