Synthetic study on telomerase inhibitor, D8646-2-6: synthesis of the key intermediate using Sn(OTf)2 or Sc(OTf)3 mediated aldol-type reaction and Stille coupling.
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.
Kanai
Akira
A
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), Chiba, Japan.
Takeda
Yoshifumi
Y
Kuramochi
Kouji
K
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D019098:Telomerase / Q000037:antagonists & inhibitors*; D017971:Tin Compounds / Q000737:chemistry*
C479141:D8646-2-6; D004791:Enzyme Inhibitors; D006027:Glycosides; D017971:Tin Compounds; D019098:Telomerase; D012538:Scandium