136612-59-4

Basic information

• Product Name: (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine
• Synonyms: (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine
• CAS NO: 136612-59-4
• Molecular Weight: 444.389
• Mol File: 136612-59-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine(136612-59-4)
• EPA Substance Registry System: (1S*,2R*,3R*)-3-phenylselanyldihydrolycorine(136612-59-4)

Safety Data

• Hazardous Substances Data: 136612-59-4(Hazardous Substances Data)

Upstream product

• 33797-51-2 eschenmoser's salt 
• 136612-48-1 (4aR*,8R*,8aR*)-8-(3',4'-methylenedioxyphenyl)-3,4,4a,7,8,8a-hexahydroisochroman-3(1H)-one 
• 136612-45-8 (E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate 
• 136612-52-7 (3aS*,4R*,7S*,7aS*)-4-hydroxy-7-(3',4'-methylenedioxyphenyl)-3a,4,7,7a-tetrahydroindolin-2-one 
• 136612-50-5 (3aS*,4S*,5R*,7aR*)-4-hydroxymethyl-5-(3',4'-methylenedioxyphenyl)-2,3,3a,4,5,7a-hexahydrobenzofuran-2-one 
• 136612-49-2 (3aS*,4S*,5R*,7S*,7aS*)-4-hydroxymethyl-7-iodo-5-(3',4'-methylenedioxyphenyl)-2,3,3a,4,5,6,7,7a-octahydrobenzofuran-2-one 
• 136612-54-9 (3aS*,4R*,7S*,7aS*)-4-(tert-butyldimethylsiloxy)-7-(3',4'-methylenedioxyphenyl)-3a,4,7,7a-tetrahydroindolin-2-one 
• 136612-55-0 (3aS*,4S*,5S*,6S*,7S*,7aR*)-4-(tert-butyldimethylsiloxy)-5,6-epoxy-7-(3',4'-methylenedioxyphenyl)-3a,4,5,6,7,7a-hexahydroindolin-2-one 
• 136612-57-2 (3aS*,4S*,5S*,6S*,7S*,7aR*)-4,5-epoxy-7-(3',4'-methylenedioxyphenyl)-2-oxo-3a,4,5,6,7,7a-hexahydroindolin-6-yl 
• 136612-46-9 (4aR*,8R*,8aR*)-8-(3',4'-methylenedioxyphenyl)-3,4,4a,7,8a-hexahydroisocoumarin 
• 136612-56-1 (3aS*,4S*,5S*,6S*,7S*,7aR*)-5,6-epoxy-7-(3',4'-methylenedioxyphenyl)-2-oxo-3a,4,5,6,7,7a-hexahydroindolin-4-yl acetate 
• 136612-44-7 (3aS*,4R*,5R*,6S*,7S*,7aS*)-5,6-dihydroxy-7-(3',4'-methylenedioxyphenyl)-4-phenylselanyl-3a,4,5,6,7,7a-hexahydroindolin-2-one 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 

Downstream Products

• 476-28-8 (±)-lycorine 

Relevant articles and documents

Potential intermediate, (±)-di-o-acetyl-3α-phenylselanyl-3,3a-dihydro-B-nor-6,7a- secolycorin-5-one for synthesis of the Amaryllidaceae alkaloid lycorine: Formal and total syntheses of (±)-lycorine

Formal and total syntheses of the Amaryllidaceae alkaloid, (±)-lycorine 1, were achieved by new synthetic routes via (±)-di-o-acetyl-3α-phenylselanyl-3,3a-dihydro-B-nor-6,7a- secolycorin-5-one 32. Namely, stereoselective intramolecular Diels-Alder reaction of triene ester 5 afforded, in good yield, the cis-lactone 6, which was converted into β(stereochemical)-hydroxy-γ-lactam 23. Oxidation of silyl ether 24 with m-chloroperbenzoic acid gave only β-(tert-butyldimethylsiloxy)-α-epoxide 25, the stereostructure of which was determined by its X-ray crystallographic analysis. Payne rearrangement of compound 25 and successive acetylation furnished α(stereochemical)-acetoxy-β(stereochemical)-epoxy γ-lactam 29, which was transformed into (±)-lycorine 1 by construction of the B ring. Formal total synthesis of (±)-lycorine 1 is also described.