Synthetic Strategies for the Construction of Enantiomeric Azanoradamantanes

Daniel Becker; Roger Nosal; Daniel L. Zabrowski; Daniel Flynn

doi:10.1016/S0040-4020(96)00973-8

Synthetic Strategies for the Construction of Enantiomeric Azanoradamantanes

Daniel Becker, Roger Nosal, Daniel L. Zabrowski, Daniel Flynn

Department of Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The amino azanoradamantane hexahydro-2,5b-methano-IH-3aS,3aa,6aa-cyclopenta-[clpyrrole-4a-amine 1and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491and SC-52490, respectively, which are of pharmaceutical interest. The key meso-azabicyclo[3.3.0] intermediate 3 was prepared via three separate routes: a [3+2] cycloaddition route, a radical cyclization/ionic cyclization route, and a reductive Pauson-Khand route.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	53
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4020(96)00973-8
State	Published - Jan 6 1997

Keywords

enantiomeric azanoradamantanes

Disciplines

Chemistry

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title = "Synthetic Strategies for the Construction of Enantiomeric Azanoradamantanes",

abstract = " The amino azanoradamantane hexahydro-2,5b-methano-IH-3aS,3aa,6aa-cyclopenta-[clpyrrole-4a-amine 1and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491and SC-52490, respectively, which are of pharmaceutical interest. The key meso-azabicyclo[3.3.0] intermediate 3 was prepared via three separate routes: a [3+2] cycloaddition route, a radical cyclization/ionic cyclization route, and a reductive Pauson-Khand route.",

keywords = "enantiomeric azanoradamantanes",

author = "Daniel Becker and Roger Nosal and Zabrowski, \{Daniel L.\} and Daniel Flynn",

year = "1997",

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doi = "10.1016/S0040-4020(96)00973-8",

language = "American English",

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journal = "Chemistry: Faculty Publications and Other Works",

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AU - Becker, Daniel

AU - Nosal, Roger

AU - Zabrowski, Daniel L.

AU - Flynn, Daniel

PY - 1997/1/6

Y1 - 1997/1/6

N2 - The amino azanoradamantane hexahydro-2,5b-methano-IH-3aS,3aa,6aa-cyclopenta-[clpyrrole-4a-amine 1and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491and SC-52490, respectively, which are of pharmaceutical interest. The key meso-azabicyclo[3.3.0] intermediate 3 was prepared via three separate routes: a [3+2] cycloaddition route, a radical cyclization/ionic cyclization route, and a reductive Pauson-Khand route.

AB - The amino azanoradamantane hexahydro-2,5b-methano-IH-3aS,3aa,6aa-cyclopenta-[clpyrrole-4a-amine 1and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491and SC-52490, respectively, which are of pharmaceutical interest. The key meso-azabicyclo[3.3.0] intermediate 3 was prepared via three separate routes: a [3+2] cycloaddition route, a radical cyclization/ionic cyclization route, and a reductive Pauson-Khand route.

KW - enantiomeric azanoradamantanes

UR - https://ecommons.luc.edu/chemistry_facpubs/14

U2 - 10.1016/S0040-4020(96)00973-8

DO - 10.1016/S0040-4020(96)00973-8

M3 - Article

VL - 53

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 1

ER -

Synthetic Strategies for the Construction of Enantiomeric Azanoradamantanes

Abstract

Keywords

Disciplines

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