126645-21-4Relevant articles and documents
Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid
Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick
, p. 2685 - 2688 (2016)
The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.
Intramolecular Pictet-Spengler Reaction of N-Alkoxytryptamines. 3. Stereoselective Synthesis of (-)-Debromoeudistomin L and (-)-O-Methyldebromoeudistomin E and Their Stereoisomers
Hermkens, Pedro H. H.,Maarseveen, Jan H. v.,Ottenheijm, Harry C. J.,Kruse, Chris G.,Scheeren, Hans W.
, p. 3998 - 4006 (2007/10/02)
The N-hydroxytrypamines 10 and 11 were converted into the N-alkoxy derivatives 32-34 (overall yield 57-72percent) by successive protection with chloroformate providing 27 and 28, reaction with functionalized chloromethyl sulfides, and deprotection with a "naked" fluoride.Intramolecular cyclization succeeded with 33 and 34 by reduction of the methyl ester with DIBAL and treatment with TFA to give diastereomeric pairs with a slight selectivity for the trans isomer (53-81percent, cis/trans ca. 35/65).Removal of the BOC group gave debromoeudistomin L ((-)-1e), its three stereoisomers (42a,b and (+)-1e), O-methyldebromoeudistomin E ((-)-1f), and its stereomer 43.
