Wan Lifeng, Tius Marcus A
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
Org Lett. 2007 Feb 15;9(4):647-50. doi: 10.1021/ol062919e.
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].
纳扎罗夫环化反应的丙二烯醚版本被用于构建马吲哚啉A和B的环戊烷二酮部分。来自纳扎罗夫环化反应的外消旋环戊烷二酮被转化为烯醇醚，该烯醇醚在曼尼希反应中与手性、非外消旋羟基呋喃吲哚啉结合。脱保护和氧化反应得到了(+)-马吲哚啉A和(+)-马吲哚啉B。[反应：见正文]
