Premium
Intramolecular (4+3) Cycloadditions of Pyrroles and Application to the Synthesis of the Core of Class II Galbulimima Alkaloids
Author(s) -
He Jiayun,
Chen Zhihua,
Li Wenfei,
Low KamHung,
Chiu Pauline
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711439
Subject(s) - cycloaddition , intramolecular force , chemistry , pyrrole , ring (chemistry) , electrophile , substructure , stereochemistry , combinatorial chemistry , organic chemistry , structural engineering , engineering , catalysis
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.