214678-53-2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 214678-52-1 {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol 
• 187931-99-3 ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 179618-33-8 ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate 
• 179618-34-9 ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate 

Downstream Products

• 214678-55-4 (R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one 
• 146236-73-9 (+)-goniodiol 
• 214678-54-3 3-Benzenesulfonyl-4-{(4R,5S)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester 

Relevant academic research and scientific papers

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.

A short and efficient total synthesis of the cytotoxic (+)-goniodiol and (+)-9-deoxygoniopypyrone

(+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have been synthesized in five steps and 75% yield respectively from C4-esters 1a and 1b. The key step of these syntheses is a triflate-sulfone coupling which allowed a rapid construction of the backbone of the title compounds as well as the efficient installation of a masked Z- acrylate moiety.