62627-31-0Relevant academic research and scientific papers
Synthetic Study on Pactamycin: Stereoselective Synthesis of the Cyclopentane Core Framework
Goto, Atsumi,Yoshimura, Satoshi,Nakao, Yuta,Inai, Makoto,Asakawa, Tomohiro,Egi, Masahiro,Hamashima, Yoshitaka,Kondo, Mitsuru,Kan, Toshiyuki
, p. 3358 - 3361 (2017)
The cyclopentane core framework 23 of pactamycin (1) was synthesized in 14 steps from symmetric cyclohexadiene 11. Our synthetic strategy features Rh-mediated catalytic desymmetrization of 10 via aziridination and then regioselective ring-opening reaction
Stereocontrolled total synthesis of sphingofungin e
Ikeuchi, Kazutada,Hayashi, Moemi,Yamamoto, Tomohiro,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
supporting information, p. 6789 - 6792 (2013/11/06)
We describe herein the asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3)2. The asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity, is described. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3) 2; TIPS = triisopropylsilyl. Copyright
Catalytic desymmetrization of cyclohexadienes by asymmetric bromolactonization
Ikeuchi, Kazutada,Ido, Shunsuke,Yoshimura, Satoshi,Asakawa, Tomohiro,Inai, Makoto,Hamashima, Yoshitaka,Kan, Toshiyuki
supporting information, p. 6016 - 6019 (2013/02/23)
Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)2PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.
Stereocontrolled total synthesis of (-)-myriocin
Inai, Makoto,Goto, Toshihiro,Furuta, Takumi,Wakimoto, Toshiyuki,Kan, Toshiyuki
scheme or table, p. 2771 - 2773 (2009/06/18)
The stereocontrolled total synthesis of (-)-myriocin 1 is reported. Optically active epoxide 9 was converted from symmetrical cyclohexadiene 8, utilizing an enzymatic kinetic resolution. The three sequential stereogenic centers of 1 were constructed by a regioselective epoxide-opening reaction and a Hofmann rearrangement. Elongation of the side chain was efficiently accomplished by the Julia-Kocienski reaction.
