Transannular diels - Alder studies on the asymmetric total synthesis of chatancin: The pyranophane approach

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2737-2740

  Toró, András ^a   L'Heureux, Alexandre ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHATANCIN; DITERPENE; FARNESOL; THROMBOCYTE ACTIVATING FACTOR;

ANIMAL; ARTICLE; CHEMISTRY; COELENTERATE; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; CNIDARIA; CRYSTALLOGRAPHY, X-RAY; DITERPENES; FARNESOL; PLATELET ACTIVATING FACTOR; STEREOISOMERISM;

EID: 0034618286     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006220z     Document Type: Article

References (23)

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2. For a recent total synthesis, see: (b) Aigner, J.; Gössinger, E.; Kählig, H.; Menz, T.; Pflugseder, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 2226-2228.
3. For isolation, see: (a) Anjaneyulu, A. S. R.; Venugopal, M. J. R. V.; Sarada, P.; Rao, G. V.; Clardy, J.; Lobkovsky, E. Tetrahedron Lett. 1998, 39, 135-138.
4. (b) The absolute configuration of 2 has not been established. The enantiomer shown is the opposite of that reported in ref 2a.
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9. Biosynthesis of 2 may involve further oxidation in ring A, followed by transketalization and an epimerization of the iso-propyl group.
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13. Used to be available from Aldrich then, now from Fluka (cat. no.): (R)-14, 37,765-1; 14800 and (S)-14, 37,767-8; 14801, respectively.
14. 3-impregnated silica column. See also refs 8 and 10.
15. See Supporting Information for experimental details.
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23. 1H NMR spectra of the mixture.