Raistrickindole A 的全合成。

The Total Synthesis of Raistrickindole A.

机构信息

School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.

Theoretical Chemistry Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar Tudósok krt. 2, Budapest 1117, Hungary.

出版信息

J Org Chem. 2022 Dec 2;87(23):16111-16114. doi: 10.1021/acs.joc.2c02033. Epub 2022 Nov 11.

DOI:10.1021/acs.joc.2c02033

PMID:36367299

Abstract

The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an -hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed -hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.

摘要

瑞斯特林吲哚 A 的全合成已经实现，从而证实了所提出的结构为 - 羟基化 DKP。在第一个但选择性较低的方法中，通过非对映异构体混合 - 羟基化二肽的环化构建了 DKP。在第二种方法中，通过羟肟酸的分子内 Mitsunobu 反应立体选择性地构建了相同的 DKP。通过立体选择性氧化环化完成了合成。