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Paper | Special issue | Vol 99, No. 2, 2019, pp.1095-1116
Published online, 12th November, 2018
DOI: 10.3987/COM-18-S(F)78
Consice Synthesis of TAN1251C

Yosuke Nagasaka, Tomohiro Asakawa, Sayaka Shintaku, Akitaka Masuda, Kosuke Matsumura, Makoto Inai, Yoshinobu Ishikawa, Masahiro Egi, Yoshitaka Hamashima, and Toshiyuki Kan*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka-shi, 422-8526, Japan


An efficient total synthesis of TAN1251C was accomplished by employing Ugi four-component condensation reaction and Dieckmann condensation to construct the spiro-fused cyclohexanone and γ-lactam ring structure. Diastereoselective reduction by side-chain-controlled hydrogenation of enamide 37 or Zn reduction of oxime 48 enabled construction of the amino group with the desired stereochemistry.