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

Zhiqiang Ma, Lin You, Chuo Chen

Research output: Contribution to journal › Article

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.

Original language	English (US)
Pages (from-to)	731-736
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.6b02266
Publication status	Published - Jan 6 2017

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Ma, Z., You, L., & Chen, C. (2017). Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter. Journal of Organic Chemistry, 82(1), 731-736. https://doi.org/10.1021/acs.joc.6b02266

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Access to Document

10.1021/acs.joc.6b02266