Synthesis of the Tetracyclic Skeleton of the Lycopodium Alkaloid Lycopladine H via a Pivotal Double Hydroformylation/Intramolecular Reductive Amination Sequence

Synthesis of the Tetracyclic Skeleton of the Lycopodium Alkaloid Lycopladine H via a Pivotal Double Hydroformylation/Intramolecular Reductive Amination Sequence

A synthesis of the complete tetracyclic framework of the structurally unique Lycopodium alkaloid lycopladine H has been accomplished using a strategy involving a double alkene hydro­formyla­tion/intra­molecular reductive amination to form the azocane and spiro-piperidine moieties of the natural prod...

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Bibliographic Details
Published in:Organic letters Vol. 17; no. 4; pp. 806 - 808
Main Authors: Chauhan, Pradeep S, Sacher, Joshua R, Weinreb, Steven M
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-02-2015
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkenes - chemistry
Amination
Azabicyclo Compounds - chemical synthesis
Lycopodium - chemistry
Molecular Structure
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Stereoisomerism
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Summary:A synthesis of the complete tetracyclic framework of the structurally unique Lycopodium alkaloid lycopladine H has been accomplished using a strategy involving a double alkene hydro­formyla­tion/intra­molecular reductive amination to form the azocane and spiro-piperidine moieties of the natural product.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503571a