Intramolecular Diels-Alder cycloadditions of fulvenes. Application to the kigelinol, neoamphilectane, and kempane skeletons

Organic Letters

Volumn 7, Issue 4, 2005, Pages 557-560

  Hong, Bor Cherng ^a   Chen, Fon Len ^a   Chen, Shang Hung ^a   Liao, Ju Hsiou ^a   Lee, Gene Hsiang ^b  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ANTIMALARIAL AGENT; ANTITRYPANOSOMAL AGENT; BENZENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; ISOKIGELINOL; KEMPEN 2; KIGELINOL; NEOAMPHILECTANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALLYLATION; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ENERGY YIELD; MOLECULAR INTERACTION; NONHUMAN; OXIDATION KINETICS; OZONOLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 14844353684     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047730m     Document Type: Article

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41. This may have occurred via a type-2 IMDA process of the fulvene. For a recent review, see: Bear, B. R.; Sparks, S. M.; Shea, K. J.; Angew. Chem., Int. Ed. 2001, 40, 820.
42. 2)].
43. Unpublished results: fulvene enone A, an analogue of 5, was prepared from (-)-limonene, and the IMDA reaction gave tricycle B.
44. Inverse-electron-demand Diels-Alder reactions usually afford a different periselectivity. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M.; Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149. For reaction with 1-azadiene, see: Mohammad B.; Mohammad A. Tetrahedron 2000, 56, 5259.
45. Inverse-electron-demand Diels-Alder reactions usually afford a different periselectivity. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M.; Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149. For reaction with 1-azadiene, see: Mohammad B.; Mohammad A. Tetrahedron 2000, 56, 5259.
46. Inverse-electron-demand Diels-Alder reactions usually afford a different periselectivity. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M.; Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149. For reaction with 1-azadiene, see: Mohammad B.; Mohammad A. Tetrahedron 2000, 56, 5259.
47. Inverse-electron-demand Diels-Alder reactions usually afford a different periselectivity. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M.; Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149. For reaction with 1-azadiene, see: Mohammad B.; Mohammad A. Tetrahedron 2000, 56, 5259.
48. 2)].
49. Purchased from Fluka [63473-60-9].
50. (a) For a recent enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by (S)-pyrrolidine derivatives, see: Melchiorre, P.; Jørgensen, A. J. Org. Chem. 2003, 68, 4151.
51. (b) Reaction of 38 with (S)-2-benzhydrylpyrrolidine gave a 4:1 mixture of the (S) isomer at the α center.
52. 2NH gave a 1:1 mixture of the (5) and (R) isomers at the α center.
53. Various attempts at the selective DIBAL-H reduction the methyl ester to the aldehyde in the presence of the ethyl ester failed. Reaction in THF gave the best selectivity but afforded the alcohol instead.
54. (a) The chloro-Prins reaction of hex-5-enal to 3-chloro-cyclohexanol system has been reported; see: Wölfling, J.; Frank, É.; Mernyák, E.; Bunkóczi, G.; Seijo, J. A. C.; Schneidera, G. Tetrahedron 2002, 58, 6851.
55. (b) For a review of the Prins reaction, see: Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661.
56. (c) For a recent review of the Pinacol-terminated Prins cyclization, see: Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143.
57. The 44 and α-isomer of 44 (i.e., 44a) were respectively prepared from 39 and 39a (S isomer on the α center) and characterized; all spectral data are consistent with this structural assignment.