Total synthesis of myriocin and mycestericin D employing Rh(II)-catalyzed CH amination followed by stereoselective alkylation
2017
Noda, Narumi | Nambu, Hisanori | Ubukata, Kana | Fujiwara, Tomoya | Tsuge, Kiyoshi | Yakura, Takayuki
Total synthesis of myriocin and mycestericin D was achieved using the Du Bois Rh(II)-catalyzed CH amination of a sulfamate and subsequent alkylation as a key step. The reaction of a sulfamate with PhI(OAc)2 and MgO in the presence of Rh2(OAc)4 gave oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of N,O-acetal using vinylmagnesium bromide in the presence of ZnCl2 proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. Myriocin and mycestericin D were synthesized from a common synthetic intermediate. This route includes the first application of the Du Bois procedure for constructing a quaternary chiral center.
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