124988-60-9

Upstream product

• 116185-13-8 (3S,4S)-3,4-Bis-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2,5-dione 
• 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 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 111194-07-1 trans-(+/-)-dihydro-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2(3H)-furanone 
• 100-44-7 benzyl chloride 
• 111266-02-5 (S)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 124988-58-5 (S)-4-<<4-(benzyloxy)-3-methoxyphenyl>methyl>dihydro-2(3H)-furanone 
• 355126-87-3 (2S,3R)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid diisopropyl ester 
• 355126-88-4 (2S,3R)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 

Downstream Products

• 61521-74-2 (3R,4R)-dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 34444-37-6 epiwikstromol 
• 34444-37-6 wikstromol 

Relevant academic research and scientific papers

Synthesis of (+)-wikstromol by double alkylation of malic acid

The synthesis of (+)-wikstromol in six steps, based on two stereoselective benzylations of unnatural malic acid derivatives, is presented. The influence of the alkyl ester on yield and selectivity in the alkylation of malic acid esters is examined.

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.