33464-73-2

Basic information

• Product Name: (-)-O-methyltrachelogenine
• Synonyms: (-)-O-methyltrachelogenine
• CAS NO: 33464-73-2
• Molecular Weight: 402.444
• Mol File: 33464-73-2.mol

Chemical Properties

• CAS DataBase Reference: (-)-O-methyltrachelogenine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-O-methyltrachelogenine(33464-73-2)
• EPA Substance Registry System: (-)-O-methyltrachelogenine(33464-73-2)

Safety Data

• Hazardous Substances Data: 33464-73-2(Hazardous Substances Data)

Upstream product

• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 116185-13-8 (3S,4S)-3,4-Bis-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2,5-dione 
• 116185-15-0 dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone 
• 111194-07-1 trans-(+/-)-dihydro-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2(3H)-furanone 
• 116185-11-6 benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate 
• 116185-12-7 2,3-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-butanedioic acid 
• 30034-49-2 β-(4-benzyloxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 4773-01-7 (3R*,4R*)-3-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 186581-53-3 diazomethane 
• 34444-37-6 wikstromol 
• 34444-37-6 epiwikstromol 

Downstream Products

• 41328-89-6 (2S,3S)-2,3-diveratryl-butane-1,2,4-triol 

Relevant articles and documents

Wikstromol, antitumor lignan from Wikstroemia foetida var. oahuensis Gray and Wikstroemia uva-ursi Gray (Thymelaeaceae)

The ethanol extracts of Wikstroemia foetida var. oahuensis and Wikstroemia uva-ursi showed antitumor activity against the P-388 lymphocytic leukemia (3PS) test system. One PS-active constituent of both plants was the lignan wikstromol. Several inactive compounds were identified as daphnoretin, pinoresinol, and syringaresinol.

TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL

The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.

Total Synthesis of (+/-)-Wikstromol

The antineoplastic prototype lignan natural product wikstromol was synthesized in racemic form by a straightforward sequence involving, as its key transformations,oxidative coupling of a carboxylic acid dianion,generation and stereoselective oxidation of a potassium enolate,and a deprotection step.The overall yield for nine steps is 29percent.Depending on the choice of oxidants for the enolate,considerable modification in the ratio of stereoisomeric products is possible.