187931-99-3

Upstream product

• 116-11-0 2-Methoxypropene 
• 179618-34-9 ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate 
• 179618-33-8 ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate 
• 77-76-9 2,2-dimethoxy-propane 
• 20698-91-3 (R)-methyl mandelate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 124876-74-0 Methyl (R)-(-)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate 
• 130115-07-0 (R)-2-(t-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 252273-46-4 trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate 
• 252273-54-4 ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate 
• 214678-52-1 {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol 
• 136778-39-7 (+)-goniofufurone 
• 96405-62-8 (5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 146236-73-9 (+)-goniodiol 
• 214678-55-4 (R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one 
• 252273-49-7 [1'R,2'R,3'R,4S]-4-(3-phenyl-1',2',3'-trihydroxypropyl)-3-phenylsulfonylbutan-4-olide 
• 252273-51-1 [1'R,2'S,3'R,5R]-5-[3'-(t-butyldimethylsilyloxy)-1',2'-isopropylidenedioxy-3'-phenylpropyl]-4-phenylsulfonylbutan-4-olide 
• 252273-48-6 trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate 
• 252273-55-5 ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate 
• 252273-57-7 ethyl (2S,3R,4S)-4-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenylbutanoate 
• 252273-58-8 trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate 
• 147527-10-4 (5S,6R)-6-[(1R,2S)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Concise stereoselective total synthesis of leiocarpin C

A simple and highly concise strategy has been developed for the stereoselective total synthesis of leiocarpin C starting from commercially available mandelic ester. The strategy utilizes the OsO4-catalyzed cis-hydroxylation and selective reduction with K-Selectride as key steps. Copyright

First total synthesis of (+)-crassalactone A

A simple and highly efficient first total synthesis of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropi

Total synthesis of antitumor Goniothalamus styryllactones

Synthesis of eight enantiopure styryllactones has been achieved from a common precursor: ethyl (2S, 3S, 4R)-4-(t-butyldimethylsilyloxy)-2,3- isopropylidenedioxy-4-phenylbutanoate 16, prepared in five steps and 65% yield from (R)-mandelic acid. Key elements for the synthesis of goniofufurone 3, goniopypyrone 4, goniobutenolides A and B (5, 6) and 7-epi-goniofufurone 7 were the introduction of the Z-acrylate moiety by a Julia coupling between 16 or its epimer in benzylic position and methyl 3-phenylsulfonyl orthopropionate 11 followed by a highly diastereoselective reduction of the resulting β-keto sulfone which sets up the last of the four contiguous asymmetric center. In the case of styryllactones 4 and 7, prior to the Julia coupling, the benzyl sterocenter of 16 was efficiently inverted by a Mitsunobu reaction. Goniodiol 1 and 9-deoxygoniopypyrone 2 were synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-9-deoxygoniopypyrone 8, thereby establishing that its structure is the following: (1R, 5R, 7S, 8S)-8-hydroxy-7-phenyl-2,6- dioxabicyclo[3.3.1] nonan-3-one.

Concise total synthesis of (+)-goniofufurone and goniobutenolides A and B

Cytotoxic styryl lactones, (+)-goniofufurone and goniobutenolides A and B have been prepared in optically and diastereometically pure form from (R)-(- )-mandelic acid via the β-hydroxy sulfone 4 as a common intermediate.