Kanai Akira, Takeda Yoshifumi, Kuramochi Kouji, Nakazaki Atsuo, Kobayashi Susumu
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), Chiba, Japan.
Chem Pharm Bull (Tokyo). 2007 Mar;55(3):495-9. doi: 10.1248/cpb.55.495.
The synthesis of the key intermediate (4) in the proposed route to D8646-2-6 is described. The aldol reaction of the carbohydrate-containing pyrone 7 with the aldehyde 6 was accomplished by using LiHMDS and Sc(OTf)3 or Sn(OTf)2. The stepwise dehydration reaction of the aldol adduct 14, followed by Stille coupling with vinyl stannane 5 which contained phosphonate gave the desired 4.