Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton

Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton

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 reducti...

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Veröffentlicht in:Organic letters 2017-07, Vol.19 (14), p.3839-3842
Hauptverfasser: Nagasaka, Yosuke, Shintaku, Sayaka, Matsumura, Kosuke, Masuda, Akitaka, Asakawa, Tomohiro, Inai, Makoto, Egi, Masahiro, Hamashima, Yoshitaka, Ishikawa, Yoshinobu, Kan, Toshiyuki
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01718