464184-44-9Relevant academic research and scientific papers
Concise asymmetric total synthesis of scyphostatin, a potent inhibitor of neutral sphingomyelinase
Fujioka, Hiromichi,Sawama, Yoshinari,Kotoku, Naoyuki,Ohnaka, Takuya,Okitsu, Takashi,Murata, Nobutaka,Kubo, Ozora,Li, Ruichuan,Kita, Yasuyuki
, p. 10225 - 10238 (2008/09/18)
The concise asymmetric total synthesis of scyphostatin has been achieved by condensation of the optically active cyclohexane unit, prepared from the commercially available 1,4-cyclohexadiene by our own method, and the side chain, prepared by the method developed by Hoye and Tennakoon (T. R. Hoye, M. A. Tennakoon, Org. Lett. 2000, 2, 1481-1483). The modification of the epoxy cyclohexenone unit was achieved in a late stage of the total synthesis, and deprotection of the primary alcohol was conducted in the final step. During the synthesis several key reactions were attained: 1) intramolecular bromoetherification of the cyclohexadiene acetal; 2) stereoselective introduction of the tertiary alcohol, 3) deprotection of the acetal function to the aldehyde by combination with silyl triflate/2,4,6-collidine and the one-pot synthesis of the disilyl aldehyde compounds, with different types of silyl groups, from the dihydroxy acetal compounds; and 4) facile deprotection of the 2,4-dimethoxyphenylmethyl (2,4DMPM) protecting group of the primary alcohol.
Concise asymmetric synthesis of a model compound, (4S,5S,6S)-6-(2,2-dimethoxy)ethyl-4,5-epoxy-6-hydroxy-2-cyclohexenone, for the cyclohexenone core of scyphostatin
Fujioka, Hiromichi,Kotoku, Naoyuki,Sawama, Yoshinari,Nagatomi, Yasushi,Kita, Yasuyuki
, p. 4825 - 4828 (2007/10/03)
The optically pure cyclohexenone core of scyphostatin (1) has been synthesized from cyclohexadiene acetal 5. The crucial aspects of our synthesis include the intramolecular bromoetherification of 5, the SeO2 oxidation of 7, and the enone formation of 13 to 4 in the final step.
