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Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4422-4431

Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of α-hydroxy epoxides

(3) Prangé, Thierry c Rodríguez, María S b Suárez, Ernesto a

a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA (Spain)

b UNIVERSIDAD DE LA LAGUNA (Spain)

c UNIVERSITÉ PARIS SACLAY (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DOUBLE BONDS;

ALCOHOLS;

ALLYL ALCOHOL; ALPHA HYDROXY EPOXIDE; ALPHA SANTONIN; CARBON; EPOXIDE; GAMMA LACTONE DERIVATIVE; HOMOALLYL ALCOHOL; OXYGEN; PHYTOALEXIN; PHYTUBERIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CYCLIZATION; DEPROTECTION REACTION; EPOXIDATION; POTATO; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; SANTONIN; SESQUITERPENES; SOLANUM; STEREOISOMERISM;

EID: 0038441471 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo034129d Document Type: Article

Times cited : (27)

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- When the crude epoxidation residue, obtained by careful elimination of the excess of dimethyldioxirane (DMD) and solvent with dry nitrogen following the standard protocol (ref 25a), was treated with dry methanol, a complex mixture resulted in which we were unable to detect any compound 37. For previous reports on the intrinsic lability of the 2,6-dioxabicyclo[3.1.0]hexane system prepared by DMD oxidation of 2,3-dihydrofurans see: (a) Timmers, C. M.; Verheijen, J. C.; Marel, A.; Boom, J. H. Synlett 1997, 851-853. (b) Johnson, W. W.; Harris, T. M.; Guengerich, F. P. J. Am. Chem. Soc. 1996, 118, 8213-8220.
- (1997) Synlett , pp. 851-853
- Timmers, C.M.¹ Verheijen, J.C.² Marel, A.³ Boom, J.H.⁴

87
- 0029836346
- When the crude epoxidation residue, obtained by careful elimination of the excess of dimethyldioxirane (DMD) and solvent with dry nitrogen following the standard protocol (ref 25a), was treated with dry methanol, a complex mixture resulted in which we were unable to detect any compound 37. For previous reports on the intrinsic lability of the 2,6-dioxabicyclo[3.1.0]hexane system prepared by DMD oxidation of 2,3-dihydrofurans see: (a) Timmers, C. M.; Verheijen, J. C.; Marel, A.; Boom, J. H. Synlett 1997, 851-853. (b) Johnson, W. W.; Harris, T. M.; Guengerich, F. P. J. Am. Chem. Soc. 1996, 118, 8213-8220.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 8213-8220
- Johnson, W.W.¹ Harris, T.M.² Guengerich, F.P.³

88
- 0037714556
- note
- 1 (ref 29).

89
- 0027953154
- Iyer, R. S.; Coles, B. F.; Raney, K. D.; Thier, R.; Guengerich, F. P.; Harris, T. M. J. Am. Chem. Soc. 1994, 116, 1603-1609.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1603-1609
- Iyer, R.S.¹ Coles, B.F.² Raney, K.D.³ Thier, R.⁴ Guengerich, F.P.⁵ Harris, T.M.⁶

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