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

Akira Kanai; Yoshifumi Takeda; Kouji Kuramochi; Atsuo Nakazaki; Susumu Kobayashi

doi:10.1248/cpb.55.495

Notes

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

Akira Kanai, Yoshifumi Takeda, Kouji Kuramochi, Atsuo Nakazaki, Susumu Kobayashi

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Keywords: aldol-type reaction, carbohydrate-containing pyrone, stille coupling, scandium triflate, tin triflate, vinyl stannane which contains phosphonate

JOURNAL FREE ACCESS

2007 Volume 55 Issue 3 Pages 495-499

DOI https://doi.org/10.1248/cpb.55.495

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Abstract

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.

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