Intramolecular (4+3) Cycloadditions of Pyrroles and Application to the Synthesis of the Core of Class II Galbulimima Alkaloids

Angewandte Chemie
Jiayun HePauline Chiu

Abstract

The first intramolecular (4+3) cycloaddition of pyrroles with epoxy enolsilanes as the electrophiles was developed and used to generate optically-enriched cycloadducts containing the nortropane substructure in good yields. Using this pyrrole cycloaddition as the key step, we achieved the asymmetric synthesis of a nortropane compound bearing the BCDEF ring structure common to the Class II galbulimima alkaloids.

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Citations

Apr 28, 2018·Chemistry : a European Journal·Tsubasa OkamotoKosuke Namba
Nov 6, 2018·Chemical Society Reviews·Zengsheng YinPauline Chiu
Apr 5, 2019·Angewandte Chemie·Barry M Trost, Zhongxing Huang
Jun 11, 2020·Chemistry, an Asian Journal·Karuppu SelvarajK C Kumara Swamy
May 6, 2021·Organic & Biomolecular Chemistry·Tanumay SarkarTharmalingam Punniyamurthy

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