Synthesis of (+)-madindoline A and (+)-madindoline B.
Synthesis of (+)-madindoline A and (+)-madindoline B.
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DOI：
10.1021/ol062919e
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发表时间：
2007-02
期刊：
影响因子：
5.2
通讯作者：
L. Wan;M. Tius
中科院分区：
文献类型：
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作者：
L. Wan;M. Tius
纳扎罗夫环化的丙二烯醚形式用于构建madindolines A和B的环戊烷二酮部分。将来自Nazarov环化的外消旋环戊烷二酮转化为烯醇醚，其在曼尼希反应中与手性非外消旋羟基呋喃并吲哚啉组合。脱保护和氧化得到（+）-madindoline A和（+）-madindoline B。[反应：见正文]。
The allene ether version of the Nazarov cyclization was used to construct the cyclopentane dione portion of madindolines A and B. The racemic cyclopentane dione from the Nazarov cyclization was converted to an enol ether that was combined with the chiral, nonracemic hydroxyfuroindoline in a Mannich reaction. Deprotection and oxidation led to (+)-madindoline A and (+)-madindoline B. [reaction: see text].