126663-64-7

Upstream product

• 91103-36-5 N-tert.-butyloxycarbonyl-L-serinal 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 20445-33-4 (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride 
• 126645-28-1 N-<(tert-butyloxy)carbonyl>-L-serinal dimethyl acetal 

Relevant academic research and scientific papers

Intramolecular Pictet-Spengler Reaction of N-Alkoxytryptamines. 3. Stereoselective Synthesis of (-)-Debromoeudistomin L and (-)-O-Methyldebromoeudistomin E and Their Stereoisomers

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.