Photoassisted Diversity-oriented Synthesis: Accessing 2,6-epoxyazocane (oxamorphan) Cores

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2014 Nov 6

PMID 25370821

Citations 7

Authors

Olga A Mukhina

N N Bhuvan Kumar

Teresa M Cowger

Andrei G Kutateladze

Affiliations

Soon will be listed here.

Abstract

The modular synthesis of photoprecursors and their photoinduced cyclization into substituted 1-benzazocanes of two distinct topologies is described. The key step producing an extended polyheterocyclic system involves the photogeneration of azaxylylenes and their subsequent intramolecular cycloaddition with furan-containing pendants tethered either via the aniline nitrogen or through the carbonyl group containing arm. The primary photoproducts-secondary or tertiary anilines which are not acylated at the nitrogen atom-undergo facile acid-catalyzed or spontaneous ring-opening-ring-closing rearrangement to yield fused polyheterocyclic structures possessing a 2,6-epoxyazocane (or oxamorphan) core.

Citing Articles

Photoinitiated Cascade for Rapid Access to Pyrroloquinazolinone Core of Vasicinone, Luotonins, and Related Alkaloids.

Reddy D, Kutateladze A Org Lett. 2019; 21(8):2855-2858.

PMID: 30933523 PMC: 6719786. DOI: 10.1021/acs.orglett.9b00858.

Photoassisted access to complex polyheterocycles containing a β-lactam moiety.

Umstead W, Mukhina O, Kutateladze A J Photochem Photobiol A Chem. 2017; 329:182-188.

PMID: 29249888 PMC: 5731649. DOI: 10.1016/j.jphotochem.2016.07.004.

Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.

Umstead W, Mukhina O, Bhuvan Kumar N, Kutateladze A Aust J Chem. 2017; 68(11):1672-1681.

PMID: 29249834 PMC: 5731653. DOI: 10.1071/CH15266.

Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.

Kuznetsov D, Mukhina O, Kutateladze A Angew Chem Int Ed Engl. 2016; 55(24):6988-91.

PMID: 27097759 PMC: 4943229. DOI: 10.1002/anie.201602288.

Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

Mukhina O, Kutateladze A J Am Chem Soc. 2016; 138(7):2110-3.

PMID: 26866604 PMC: 5578731. DOI: 10.1021/jacs.5b12690.

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