Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton
Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton
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通过 Azaspiro 骨架的非对映选择性构建 TAN1251C 的全合成
DOI：
10.1021/acs.orglett.7b01718
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Kan T.
中科院分区：
文献类型：
--
作者：
Nagasaka Y;Shintaku S;Matsumura K;Masuda A;Asakawa T;Inai M;Egi M;Hamashima Y;Ishikawa Y;Kan T.
采用Ugi四组分积累反应和Dieckmann缩合反应构建了旋合环己酮和γ-内酰胺环，实现了TAN1251C的高效全合成。通过侧链控制的珐琅质氢化或锌还原肟23的非对映选择性还原使氨基具有所需的立体化学结构。
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 enamide15or Zn reduction of oxime23enabled construction of the amino group with the desired stereochemistry.