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Parallel modification of tropane alkaloids

Parallel modification of tropane alkaloids
Parallel modification of tropane alkaloids
Various tropane alkaloids have been prepared by structural modification of the readily available natural product, scopolamine 1. Reaction of isocyanates with 6,7-dehydrotropine 5 provided a number of urethanes 6a-e. Reductive amination of tropinone 7 and subsequent reaction with isocyanates provided ureas 9a-f. Mitsunobu inversion of the C-3 alcohol of tropine 10 afforded the epimeric ester 11.
mitsunobu reaction, derivatives, reagents
0040-4039
1975-1977
Aberle, Nicholas S.
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Ganesan, A.
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Lambert, John N.
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Saubern, Simon
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Smith, Reg
12d65bbc-b3e4-403d-9dec-1b44adda3c9b
Aberle, Nicholas S.
f6565dd9-007e-4b74-8be7-4926a5fd30f8
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Lambert, John N.
9e79f7cd-8050-4ff2-94b0-60187e0ba476
Saubern, Simon
82dad27a-5023-4441-9682-5b5f3aaebb1c
Smith, Reg
12d65bbc-b3e4-403d-9dec-1b44adda3c9b

Aberle, Nicholas S., Ganesan, A., Lambert, John N., Saubern, Simon and Smith, Reg (2001) Parallel modification of tropane alkaloids. Tetrahedron Letters, 42 (10), 1975-1977. (doi:10.1016/S0040-4039(01)00028-4).

Record type: Article

Abstract

Various tropane alkaloids have been prepared by structural modification of the readily available natural product, scopolamine 1. Reaction of isocyanates with 6,7-dehydrotropine 5 provided a number of urethanes 6a-e. Reductive amination of tropinone 7 and subsequent reaction with isocyanates provided ureas 9a-f. Mitsunobu inversion of the C-3 alcohol of tropine 10 afforded the epimeric ester 11.

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More information

Published date: 2001
Keywords: mitsunobu reaction, derivatives, reagents

Identifiers

Local EPrints ID: 19373
URI: https://eprints.soton.ac.uk/id/eprint/19373
ISSN: 0040-4039
PURE UUID: c79e5b0e-6280-453a-b636-9266e3a1f2de

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Date deposited: 13 Feb 2006
Last modified: 17 Jul 2017 16:31

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Contributors

Author: Nicholas S. Aberle
Author: A. Ganesan
Author: John N. Lambert
Author: Simon Saubern
Author: Reg Smith

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