Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine
Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine
(+)-Allomatrine has been synthesised using an imino-aldol reaction and N-acyliminium cyclisation as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enables the staged formation of 3 C—C bonds, a C—N bond and the four stereogenic centres within the target.
4596-4599
Watkin, Samuel V.
e30119fd-05e0-4a0e-9c35-e393e8a59ab2
Camp, Nicholas P.
4f21b310-272b-4c01-8c6b-60d36046cb28
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
27 August 2013
Watkin, Samuel V.
e30119fd-05e0-4a0e-9c35-e393e8a59ab2
Camp, Nicholas P.
4f21b310-272b-4c01-8c6b-60d36046cb28
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Watkin, Samuel V., Camp, Nicholas P. and Brown, Richard C.D.
(2013)
Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine.
Organic Letters, 15 (17), .
(doi:10.1021/ol402198n).
Abstract
(+)-Allomatrine has been synthesised using an imino-aldol reaction and N-acyliminium cyclisation as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enables the staged formation of 3 C—C bonds, a C—N bond and the four stereogenic centres within the target.
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Published date: 27 August 2013
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 356452
URI: http://eprints.soton.ac.uk/id/eprint/356452
ISSN: 1523-7060
PURE UUID: 623e90ac-895c-4e67-825b-4d19922d7264
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Date deposited: 30 Sep 2013 14:47
Last modified: 15 Mar 2024 02:53
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Author:
Samuel V. Watkin
Author:
Nicholas P. Camp
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