187931-99-3Relevant academic research and scientific papers
Concise stereoselective total synthesis of leiocarpin C
Chandra Rao, Dasireddi,Shekhar, Vanam,Kumar Reddy, Dorigondla,Chinnababu, Baggu,Venkateswarlu, Yenamandra
, p. 2179 - 2184 (2014/01/06)
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
Shekhar,Kumar Reddy,Suresh,Chanti Babu,Venkateswarlu
scheme or table, p. 946 - 948 (2010/04/29)
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
Surivet, Jean-Philippe,Vatele, Jean-Michel
, p. 13011 - 13028 (2007/10/03)
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
Surivet, Jean-Philippe,Vatele, Jean-Michel
, p. 4373 - 4376 (2007/10/03)
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.
