Synthesis of 2-Azabicyclo[3.3.1]nonanes

Josep Bonjoch; Faïza Diaba; Ben Bradshaw

doi:10.1055/s-0030-1258420

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Synthesis 2011(7): 993-1018
DOI: 10.1055/s-0030-1258420

REVIEW

Synthesis of 2-Azabicyclo[3.3.1]nonanes

Josep Bonjoch*, Faïza Diaba, Ben Bradshaw
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, IBUB, Av. Joan XXIII s/n, 08028 Barcelona, Spain
Fax: +34(93)4024539; e-Mail: josep.bonjoch@ub.edu;

Further Information

Publication History

Received 5 November 2010
Publication Date:
03 February 2011 (online)

Abstract
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Abstract

This review highlights advances in the synthesis of morphan compounds from 1980 to the present day.

1 Introduction

2 Synthetic Approaches from Carbocyclic Compounds

2.1 Aminocyclization Processes Forming the C(1)-N Bond

2.1.1 From Amino Alkenes

2.1.2 From Amino Ketones

2.1.3 By Amine Alkylation

2.1.4 By Amino Conjugate Addition upon Enones

2.2 Aminocyclization Processes Forming the N-C(3) Bond

2.3 Cyclization Processes Forming the C(3)-C(4) Bond

2.4 Cyclization Processes Forming the C(4)-C(5) Bond

2.4.1 Aldol Reactions

2.4.2 Piperidine Ring Closure by a Heck Reaction

2.4.3 Alkenylation of Enolates

2.4.4 Radical Cyclizations

2.4.5 Miscellaneous Approaches

3 Synthetic Approaches from Piperidine Derivatives

3.1 Cyclization upon Iminium Ions Forming the C(1)-C(8) Bond

3.2 Cyclization Processes Forming the C(5)-C(6) Bond

3.3 Cyclization Processes Forming the C(6)-C(7) Bond

4 Cascade Processes

5 Rearrangements

6 Synthesis of 5-Phenylmorphans

7 Conclusions

Key words

alkaloids - carbocycles - natural products - piperidines - ring closure

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21

Syntheses in which an aromatic ring is key to the morphan ring formation are not included in this review.