Towards the synthesis of Paulitin: New insights into the enyne-metathesis mechanism

Synlett

Volumn , Issue 15, 2005, Pages 2379-2381

  Vedrenne, Emeline ^a   Royer, Frédérique ^a   Oble, Julie ^a   El Kaïm, Laurent ^a   Grimaud, Laurence ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

Author keywords

1,3 dienes; Alkyne; Mechanism; Metathesis; Steric hindrance

Indexed keywords

PAULITIN; SESQUITERPENE LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLIZATION; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; LACTONIZATION; RING CLOSING METATHESIS; STEREOSPECIFICITY;

EID: 25444456411     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872261     Document Type: Article

References (18)

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2. (b) This molecule had been previously isolated from Ambrosia dumosa in 1979, see: Seaman, F. C.; Mabry, T. J. Rev. Latinoam. Quim. 1979, 10, 85.
3. Likhitwitayawuld, K.; Angerhofer, C. K.; Cordell, G. A.; Pezzuto, J. M.; Ruangrungsi, N. J. Nat. Prod. 1993, 56, 30.
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8. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
9. For a discussion concerning enyne metathesis mechanism, see: (a) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
10. (b) Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2518.
11. (c) For a more recent study, see: Galan, B. R.; Giessert, A. J.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 5762.
12. Recently, in contrast to our results, Diver and co-workers suggested that more substituted alkynes gave faster reactions: Galan, B. R.; Giessert, A. J.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 5762.
13. According to NMR spectra, regioisomer 2 seemed to be isolated as one single stereoisomer whose configuration was not determined.
14. (a) This could be done in a one-step procedure according to our previous work (see ref. 8b) or in a two-step procedure (see ref. 8c).
15. (b) Royer, F.; Vilain, C.; El Kaïm, L.; Grimaud, L. Org. Lett. 2003, 5, 2007.
16. (c) Cesati, R. R.; De Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96.
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