Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C

[Display omitted] The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyl...

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Bibliographic Details
Published in:Tetrahedron letters 2016-03, Vol.57 (11), p.1270-1272
Main Authors: Archer, Susanna G., Csatayová, Kristína, Davies, Stephen G., Fletcher, Ai M., Roberts, Paul M., Thomson, James E.
Format: Article
Language:English
Subjects:
3-epi-Xestoaminol C
Asymmetry
Conjugate addition
Conjugates
Derivatives
Lithium
Natural product
Natural products
Purification
Synthesis
Tetrahedrons
Xestoaminol C
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Summary:[Display omitted] The asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C is reported. The synthesis employs diastereoselective aminohydroxylation of tert-butyl crotonate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a diastereoselective reduction protocol as the key stereodefining steps. The synthetic sample of the natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.02.021