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0030009927
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Kocienski and co-workers have recently described a particularly elegant synthesis of (+)-herboxidiene A, a diastereoisomer of the natural product (see N. D. Smith, P. J. Kocienski and S. D. A. Street, Synthesis, 1996, 652).
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Smith, N.D.1
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3
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33748659188
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personal communication
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Workers at Sandoz Agro AG (Basel) and the University of Geneva have recently re-isolated herboxidiene and, using a combination of X-ray analysis, degradation and asymmetric synthesis of appropriate fragments have determined the relative and absolute configuration of the natural product (Dr A. J. F. Edmunds, personal communication to M. G. B.). However, at the time of writing, details of the full structure of herboxidiene are not available.
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Edmunds, A.J.F.1
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M. G. Banwell, C. T. Bui, G. W. Simpson and K. G. Watson, Chent. Commun., 1996, 723.
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to be submitted
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M. G. Banwell, C. T. Bui, G. W. Simpson and K. G. Watson, J. Chem. Soc., Perkin Trans. 1, to be submitted.
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J. Chem. Soc., Perkin Trans. 1
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A. I. Meyers, K. A. Babiak, A. L. Campbell, D. L. Comins, M. P. Fleming, R. Henning, M. Heuschmann, J. P. Hudspeth, J. M. Kane, P. J. Reider, D. M. Roland, K. Shimizu, K. Tomioka and R. D. Walkup, J. Am. Chem. Soc., 1983, 105, 5015.
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12
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The enantiomer of compound 10 [viz. (+)-10] has been reported previously (a) S. D. Burke, D. M. Armistead, F. J. Schoenen and J. M. Fevig, Tetrahedron, 1986, 42, 2787;
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(b) S. D. Burke, A. D. Piscopio, B. E. Marron, M. A. Matulenko and G. Pan, Tetrahedron Lett., 1991, 32, 857.
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(a) S. R. Schow, J. D. Bloom, A. S. Thompson, K. N. Winzenberg and A. B. Smith III, J. Am. Chem. Soc., 1986, 108, 2662;
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(b) P. Wipf in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 5, pp. 840-847.
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