An efficient synthesis of semiplenamide C

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5547-5549

  Davies, Iwan R ^a   Cheeseman, Matt ^a   Niyadurupola, D Gangani ^a   Bull, Steven D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

Elimination; N Acyl oxazolidin 2 one; Natural product; syn Aldol

Indexed keywords

AMIDE; ANANDAMIDE; SEMIPLENAMIDE C; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CYANOBACTERIUM; DEHYDRATION; DRUG SYNTHESIS; METABOLITE; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 22144484527     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.027     Document Type: Article

References (11)

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6. 3); H. Allali, B. Tabti, C. Alexandre, and F. Huet Tetrahedron: Asymmetry 15 2004 1331
7. These conditions have been used previously for asymmetric syn-aldol reactions using imidazolidin-2-one derived glycine enolates, see: S. Caddick, N.J. Parr, and M.C. Pritchard Tetrahedron Lett. 41 2000 5963
8. 4).
9. (2′,3′) coupling constant for anti-aldols of this type are normally >7.0 Hz; see: F.J.P. Feuillet, G. Niyadurupola, R. Green, M. Cheeseman, and S.D. Bull Synlett 2005 1090
10. This type of retro-aldol pathway has been exploited previously for the asymmetric synthesis of enantiopure cyclopropane carboxaldehydes see: M. Cheeseman, F.J.P. Feuillet, and S.D. Bull Chem. Commun. 2005 2372
11. 3); all other spectroscopic data for (S)-1c were identical to that published in Ref. 2.