Stereoselective Synthesis of Highly Functionalized 5- and 6-Membered Aminocyclitols Starting with a Readily Available 2-Azetidinone

Raghavendra Achary; Hyeong Rae Kim; Hyeon-Kyu Lee

doi:10.1021/acs.joc.9b00239

Stereoselective Synthesis of Highly Functionalized 5- and 6-Membered Aminocyclitols Starting with a Readily Available 2-Azetidinone

J Org Chem. 2019 Apr 5;84(7):4263-4272. doi: 10.1021/acs.joc.9b00239. Epub 2019 Mar 26.

Authors

Raghavendra Achary¹, Hyeong Rae Kim^{1

2}, Hyeon-Kyu Lee^{1

2}

Affiliations

¹ Korea Chemical Bank , Korea Research Institute of Chemical Technology , P.O. Box 107, Yuseong, Daejeon 305-600 , Korea.
² Department of Medicinal Chemistry and Pharmacology , University of Science and Technology , 113 Gwahango , Yuseong, Daejeon 305-333 , Korea.

PMID: 30870595
DOI: 10.1021/acs.joc.9b00239

Abstract

Stereoselective transformations of 4-vinyl-2-azetidinone derivative 4 into a variety of highly functionalized 6- and 5-membered carbocyclic compounds 7 and 9 were carried out using sequences involving sequential C1-N bond cleavage and Ru-catalyzed ring-closing metathesis. The derived carbocycles were further transformed into polyhydroxylated 6- and 5-membered aminocyclitols.

Publication types

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