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Synthesis 2011(7): 993-1018
DOI: 10.1055/s-0030-1258420
DOI: 10.1055/s-0030-1258420
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2-Azabicyclo[3.3.1]nonanes
Further Information
Received
5 November 2010
Publication Date:
03 February 2011 (online)
Publication History
Publication Date:
03 February 2011 (online)
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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Syntheses in which an aromatic ring is key to the morphan ring formation are not included in this review.