Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.
Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.
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DOI：
10.1021/jo2000308
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发表时间：
2011-03-18
影响因子：
3.6
通讯作者：
Danheiser, Rick L.
中科院分区：
文献类型：
--
作者：
Mak, Xiao Yin;Crombie, Aimee L.;Danheiser, Rick L.
描述了用于合成苯并稠合氮杂环的两阶段“串联策略”，该策略对于构建苯环上具有高水平取代的系统特别有用。该策略的第一阶段涉及基于环丁烯酮与炔酰胺反应的苯并环化。该级联过程通过一系列四个周环反应进行，并提供多取代的苯胺衍生物，该衍生物可以在氮邻位上带有多种官能化取代基。在串联策略的第二阶段，闭环复分解生成氮杂环。这种两步序列提供了高效获得高度取代的二氢喹啉、苯并氮杂、苯并佐辛和相关苯并稠合氮杂环系统的途径。描述了该化学在抗癌剂 (+)-FR900482 和 (+)-FR66979 的简明正式全合成中的应用。
A two-stage “tandem strategy” for the synthesis of benzofused nitrogen heterocycles is described that is particularly useful for the construction of systems with a high level of substitution on the benzenoid ring. The first stage in the strategy involves a benzannulation based on the reaction of cyclobutenones with ynamides. This cascade process proceeds via a sequence of four pericyclic reactions and furnishes a multiply substituted aniline derivative which can bear a variety of functionalized substituents at the position ortho to the nitrogen. In the second stage of the tandem strategy, ring closing metathesis generates the nitrogen heterocyclic ring. This two-step sequence provides efficient access to highly substituted dihydroquinolines, benzazepines, benzazocines, and related benzofused nitrogen heterocyclic systems. The application of this chemistry in a concise formal total synthesis of the anticancer agents (+)- FR900482 and (+)-FR66979 is described.
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影响因子：
3.6
作者：
CABRI, W;DEBERNARDINIS, S;SANTI, R
通讯作者：
SANTI, R
影响因子：
15
作者：
Crimmins, MT;King, BW;Tabet, EA
通讯作者：
Tabet, EA
影响因子：
1.8
作者：
DANHEISER, RL;CASEBIER, DS;LOEBACH, JL
通讯作者：
LOEBACH, JL
影响因子：
16.6
作者：
Coste, Alexis;Karthikeyan, Ganesan;Evano, Gwilherm
通讯作者：
Evano, Gwilherm
影响因子：
3.6
作者：
Crimmins, MT;King, BW;Chaudhary, K
通讯作者：
Chaudhary, K