Organic Letters
Organic Letters
5 years ago

Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton

Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton
Makoto Inai, Masahiro Egi, Yoshinobu Ishikawa, Tomohiro Asakawa, Yoshitaka Hamashima, Akitaka Masuda, Kosuke Matsumura, Sayaka Shintaku, Yosuke Nagasaka, Toshiyuki Kan
An efficient total synthesis of TAN1251C was accomplished by employing a Ugi four-component accumulation reaction and a Dieckmann condensation to construct the spiro-fused cyclohexanone and γ-lactam ring. Diastereoselective reduction by side-chain-controlled hydrogenation of enamide 15 or Zn reduction of oxime 23 enabled construction of the amino group with the desired stereochemistry.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01718

DOI: 10.1021/acs.orglett.7b01718

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