Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step

Angewandte Chemie - International Edition

Volumn 44, Issue 11, 2005, Pages 1733-1735

  Davies, Huw M L ^a   Walji, Abbas M ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

C H activation; Enantioselectivity; Natural products; Terpenoids; Total synthesis

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CATALYSTS; RHODIUM; SYNTHESIS (CHEMICAL);

EROGORGIAENE; RHODIUM CATALYSTS;

REACTION KINETICS;

DITERPENE; EROGORGIAENE;

ARTICLE; KINETICS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DITERPENES; KINETICS;

EID: 17044429442     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462227     Document Type: Article

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7. Selected examples: Pseudopterosins: E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777-12782; Pseudopteroxazole: J. P. Davidson, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 13486-13489; Elisabethins: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681; Colombiasin A: a) K. C. Nicolaou, S. A. Synder in Classics in Total Synthesis II, Wiley-Interscience, Weinheim, 2003, pp. 423-442; b) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Chem. Eur. J. 2001, 7, 5359-5371; Colombiasin A and Elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308; Angew. Chem. Int. Ed. 2003, 42, 1267-1270.
8. Selected examples: Pseudopterosins: E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777-12782; Pseudopteroxazole: J. P. Davidson, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 13486-13489; Elisabethins: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681; Colombiasin A: a) K. C. Nicolaou, S. A. Synder in Classics in Total Synthesis II, Wiley-Interscience, Weinheim, 2003, pp. 423-442; b) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Chem. Eur. J. 2001, 7, 5359-5371; Colombiasin A and Elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308; Angew. Chem. Int. Ed. 2003, 42, 1267-1270.
9. Selected examples: Pseudopterosins: E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777-12782; Pseudopteroxazole: J. P. Davidson, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 13486-13489; Elisabethins: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681; Colombiasin A: a) K. C. Nicolaou, S. A. Synder in Classics in Total Synthesis II, Wiley-Interscience, Weinheim, 2003, pp. 423-442; b) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Chem. Eur. J. 2001, 7, 5359-5371; Colombiasin A and Elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308; Angew. Chem. Int. Ed. 2003, 42, 1267-1270.
10. Selected examples: Pseudopterosins: E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777-12782; Pseudopteroxazole: J. P. Davidson, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 13486-13489; Elisabethins: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681; Colombiasin A: a) K. C. Nicolaou, S. A. Synder in Classics in Total Synthesis II, Wiley-Interscience, Weinheim, 2003, pp. 423-442; b) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Chem. Eur. J. 2001, 7, 5359-5371; Colombiasin A and Elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308; Angew. Chem. Int. Ed. 2003, 42, 1267-1270.
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17. O. O. Gerlits, P. Coppens, Private Communication, 2004. CCDC-242585 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.a-c.uk/data_request/cif.