Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter

Zhiqiang Ma; Lin You; Chuo Chen

doi:10.1021/acs.joc.6b02266

Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter

J Org Chem. 2017 Jan 6;82(1):731-736. doi: 10.1021/acs.joc.6b02266. Epub 2016 Dec 20.

Authors

Zhiqiang Ma¹, Lin You¹, Chuo Chen¹

Affiliation

¹ Department of Biochemistry, The University of Texas Southwestern Medical Center , 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.

Abstract

Stereoselective construction of the 1,3-diazaspiro[4.4]nonane core skeleton of massadine and related dimeric pyrrole-imidazole alkaloids is a synthetic challenge. We describe herein the synthesis of all C13/14 diastereomers of this spiro molecule through controlled oxidation and epimerization of the C13 spirocenter under mild acidic conditions.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Molecular Conformation
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Heterocyclic Compounds, 4 or More Rings
Spiro Compounds

Grants and funding

R01 GM079554/GM/NIGMS NIH HHS/United States