Total synthesis of the cp molecules cp-225,917 and cp-263,114 - Part 2: Evolution of the final strategy

Angewandte Chemie - International Edition

Volumn 38, Issue 11, 1999, Pages 1676-1678

  Nicolaou, K C ^a,b   Baran, Phil S ^a,b   Zhong, Yong Li ^a,b   Fong, Kin Chiu ^a,b   He, Yun ^a,b   Yoon, Won Hyung ^a,b   Choi, Ha Soon ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Domino reactions; Natural products; Polycycles; Total synthesis

Indexed keywords

CP 225917; CP 263114; HYPOCHOLESTEROLEMIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033152137     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1676::AID-ANIE1676>3.0.CO;2-T     Document Type: Article

References (21)

1. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669.
2. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669.
3. T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; 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.
4. T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; 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.
5. For the chemistry and biology of the CP molecules and studies directed towards their synthesis, see the preceding communication and references cited therein.
6. a) K. C. Nicolaou, M. W. Härter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194;
7. a) K. C. Nicolaou, M. W. Härter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194;
8. b) K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821.
9. b) K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821.
10. c) K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong, Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
11. c) K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong, Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
12. Throughout the course of this work we found that intermediates with the pyran motif are much more stable and behave better on silica gel than their hydrated counterparts corresponding to the CP-225,917 structure (2).
13. M. J. V. de Oliveira Baptista, A. G. M. Barrett, D. H. R. Barton, M. Girijavallabhan, R. C. Jennings, J. Kelly, V. J. Papadimitriou, J. V. Turner, N. A. Usher, J. Chem. Soc. Perkin Trans. 1 1977, 1477.
14. a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155;
15. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277;
16. c) S. D. Meyers. S. L. Schreiber, J. Org. Chem. 1994, 59, 7549.
17. K. C. Nicolaou, Y. He, K. C. Fong, W. H. Yoon, H.-S. Choi, Y.-L. Zhong, P. S. Baran, Org. Lett. 1999, 1, in press; see also the discussion in reference [1].
18. Although reference [6] reports the use of DDQ to effect this transformation, only decomposition was observed under these conditions. After an extensive search, p-chloroanil was identified as the most suitable reagent to accomplish this conversion, presumably as a consequence of its milder nature.
19. F. G. West, J. A. Bender in Encyclopedia of Reagents for Organic Synthesis, Vol. 5 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, p. 3132.
20. Model studies on compounds with only the maleic anhydride moiety have shown that this delicate functionality is rapidly opened with LiOH; this seemingly detrimental outcome can be reversed simply by using mildly acidic conditions.
21. Synthetic 1 and 2 exhibited identical chromatographic and spectroscopic data to those of authentic samples.