Asymmetric Synthesis of (-)-Pterocarine and (-)-Galeon via Chiral Phase Transfer-Catalyzed Atropselective Formation of Diarylether Cyclophane Skeleton

Qiang Ding; Qiuyan Wang; Huan He; Qian Cai

doi:10.1021/acs.orglett.7b00570

Asymmetric Synthesis of (-)-Pterocarine and (-)-Galeon via Chiral Phase Transfer-Catalyzed Atropselective Formation of Diarylether Cyclophane Skeleton

Org Lett. 2017 Apr 7;19(7):1804-1807. doi: 10.1021/acs.orglett.7b00570. Epub 2017 Mar 27.

Authors

Qiang Ding¹, Qiuyan Wang^{1

2}, Huan He^{1

2}, Qian Cai¹

Affiliations

¹ College of Pharmacy, Jinan University , No. 601 Huangpu Avenue West, Guangzhou, 510632, China.
² College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology , Shijiazhuang 050018, China.

PMID: 28345937
DOI: 10.1021/acs.orglett.7b00570

Abstract

Pterocarine and galeon are typical examples of diarylether heptanoids (DAEHs) with planar chirality due to the strictly constrained conformations in their molecular skeletons. The characterized oxa[1,7]metapara-cyclophane motifs in DAEHs impose great challenges for their enantioselective synthesis. The asymmetric syntheses of (-)-pterocarine and (-)-galeon are demonstrated by employing a chiral phase transfer-catalyzed highly enantioselective S_NAr cyclization as the key step for the formation of a diarylether cyclophane skeleton.

Publication types

Research Support, Non-U.S. Gov't