A Novel Approach to the CP-225,917 and CP-263,114 Core

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2821-2823

  Nicolaou, K C ^a,b   Postema, Maarten H D ^a,b   Miller, Neil D ^a,b   Yang, Guang ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cyclizations; Cyclopropanations; Natural products; Rearrangements

Indexed keywords

EID: 0032491844     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199728211     Document Type: Article

References (22)

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2. T. T. Dabrah, H. J. Harwood, Jr., L. H. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, J. Antibiot. 1997, 50, 1.
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5. While this work was in progress a preliminary report appeared outlining a strategy for the preparation of the CP core using the divinylcyclopropane rearrangement: H. M. L. Davies, R. Calvo, G. Ahmed, Tetrahedron Lett. 1997, 38, 1737.
6. For recent insights on this reaction see: a) L. J. Brzezinski, S. A. Rafel, J. W. Leahy, J. Am. Chem. Soc. 1997, 119, 4317; b) S. Rafel, J. W. Leahy, J. Org. Chem. 1997, 62, 1521, and references therein.
7. For recent insights on this reaction see: a) L. J. Brzezinski, S. A. Rafel, J. W. Leahy, J. Am. Chem. Soc. 1997, 119, 4317; b) S. Rafel, J. W. Leahy, J. Org. Chem. 1997, 62, 1521, and references therein.
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11. For leading references to rhodium carbenoid chemistry, see: a) D. F. Taber, Y. Song, J. Org. Chem. 1996, 61, 6706; b) H. M. L. Davies in Comprehensive Organic Synthesis, Vol. 4 (Ed.: B. M. Trost), Pergamon, New York, 1991, p. 1031.
12. The stereochemistry of compound 11 was assigned through the use of COSY, NOESY, ROESY, and HMQC NMR experiments on the corresponding primary alcohol obtained by reduction (DIBAL 2.2 equiv).
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17. P. A. Wender, M. P. Filosa, J. Org. Chem. 1976, 41, 3490; for a review on this type of reaction see: E. Piers, Comprehensive Organic Synthesis, Vol. 5 (Ed.: B. M. Trost), Pergamon, New York, 1991, p. 971.
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22. These operations were performed on an SGI Indigo-2 workstation using the program Insight II (Biosym Technologies, Inc., San Diego, CA)