Approach towards an EPC synthesis of nodusmicin - III. Preparation of the oxygen bridged decalin part of nodusmicin

Tetrahedron

Volumn 53, Issue 9, 1997, Pages 3083-3100

  Gössinger, Edda ^a   Graupe, Michael ^a   Kratky, Christoph ^b   Zimmermann, Kurt ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0031550827     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00065-3     Document Type: Article

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61. 29 Winstein, S.; Smith, S.; Darwish, D. J. Am. Chem. Soc. 1959, 81, 5511-5512; Braun, R.; SaueR, J. Chem. Ber. 1986, 119, 1269-1274; Pocker, Y.; Ciula, J.C. J. Am. Chem. Soc. 1989, 111, 4728-4735; Waldmann, H. Angew. Chem. 1991, 103, 1335-1337 (Int. 1991, 30, 1306); Forman, M.A.; Dailey, W.P. J. Am. Chem. Soc. 1991, 113, 2761-2762; Grieco, P.A. Aldrichim. Acta 1991, 24, 59-65; Srisiri, W.; Padias, A.B.; Hall, H.K. Jr. J. Org. Chem. 1993, 58, 4185-4186; Grieco J. Am. Chem. Soc. 1993, 115, 6078-6093; Pagui, R.M.; Kabalka, G.W.; Bains, S.; Plesco, M.; Wilson, J.; Bartmess, J. J. Org. Chem. 1993, 58, 3130-3133; Saraswathy, V.G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665-4670; Grieco, P.A. "Organic Chemistry in Lithium Perchlorate / Diethylether" Chemistry, Its Language, Its State of Art, Kisakuerek (Ed.), Verl. HeLv. Chim. Acta, 1993, pp. 133-146.
62. 29 Winstein, S.; Smith, S.; Darwish, D. J. Am. Chem. Soc. 1959, 81, 5511-5512; Braun, R.; SaueR, J. Chem. Ber. 1986, 119, 1269-1274; Pocker, Y.; Ciula, J.C. J. Am. Chem. Soc. 1989, 111, 4728-4735; Waldmann, H. Angew. Chem. 1991, 103, 1335-1337 (Int. 1991, 30, 1306); Forman, M.A.; Dailey, W.P. J. Am. Chem. Soc. 1991, 113, 2761-2762; Grieco, P.A. Aldrichim. Acta 1991, 24, 59-65; Srisiri, W.; Padias, A.B.; Hall, H.K. Jr. J. Org. Chem. 1993, 58, 4185-4186; Grieco J. Am. Chem. Soc. 1993, 115, 6078-6093; Pagui, R.M.; Kabalka, G.W.; Bains, S.; Plesco, M.; Wilson, J.; Bartmess, J. J. Org. Chem. 1993, 58, 3130-3133; Saraswathy, V.G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665-4670; Grieco, P.A. "Organic Chemistry in Lithium Perchlorate / Diethylether" Chemistry, Its Language, Its State of Art, Kisakuerek (Ed.), Verl. HeLv. Chim. Acta, 1993, pp. 133-146.
63. 29 Winstein, S.; Smith, S.; Darwish, D. J. Am. Chem. Soc. 1959, 81, 5511-5512; Braun, R.; SaueR, J. Chem. Ber. 1986, 119, 1269-1274; Pocker, Y.; Ciula, J.C. J. Am. Chem. Soc. 1989, 111, 4728-4735; Waldmann, H. Angew. Chem. 1991, 103, 1335-1337 (Int. 1991, 30, 1306); Forman, M.A.; Dailey, W.P. J. Am. Chem. Soc. 1991, 113, 2761-2762; Grieco, P.A. Aldrichim. Acta 1991, 24, 59-65; Srisiri, W.; Padias, A.B.; Hall, H.K. Jr. J. Org. Chem. 1993, 58, 4185-4186; Grieco J. Am. Chem. Soc. 1993, 115, 6078-6093; Pagui, R.M.; Kabalka, G.W.; Bains, S.; Plesco, M.; Wilson, J.; Bartmess, J. J. Org. Chem. 1993, 58, 3130-3133; Saraswathy, V.G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665-4670; Grieco, P.A. "Organic Chemistry in Lithium Perchlorate / Diethylether" Chemistry, Its Language, Its State of Art, Kisakuerek (Ed.), Verl. HeLv. Chim. Acta, 1993, pp. 133-146.
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66. α-radiation, Absolute structure: η = 1.4(2).
67. 31 Crystal Structure Data for 1, 3, 4, 5 and (±)-17 have been deposited at the Cambridge Crystallographic Data Centre.
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