Xu, Qihai; Dupper, Nathan J; Smaligo, Andrew J; Fan, Yi Chiao; Cai, Lingchao; Wang, Zhiming; Langenbacher, Adam D; Chen, Jau-Nian; Kwon, Ohyun

doi:10.1021/acs.orglett.8b02489

Download PDF

Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α‑Methylallenoates

2018

Published Web Location

https://doi.org/10.1021/acs.orglett.8b02489

Abstract

P-Chiral [2.2.1] bicyclic phosphines (HypPhos catalysts) have been applied to reactions between α-alkylallenoates and imines, producing guvacine derivatives. These HypPhos catalysts were assembled from trans-4-hydroxyproline, with the modular nature of the synthesis allowing variations of the exocyclic P and N substituents. Among them, exo-( p-anisyl)-HypPhos was most efficacious for [4 + 2] annulations between ethyl α-methylallenoate and imines. Through this method, ( R)-aplexone was identified as being responsible for the decrease in the cellular levels of cholesterol.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.

Main Content

For improved accessibility of PDF content, download the file to your device.

UCLA

Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α‑Methylallenoates

Published Web Location