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

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

Author keywords

Domino reactions; Natural products; Polycycles; Total synthesis

Indexed keywords

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

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
Times cited : (100)

References (21)
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    • 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.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1669
  • 3
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    • 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.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1594
    • Dabrah, T.T.1    Kaneko, T.2    Massefski W., Jr.3    Whipple, E.B.4
  • 5
    • 0344364699 scopus 로고    scopus 로고
    • note
    • For the chemistry and biology of the CP molecules and studies directed towards their synthesis, see the preceding communication and references cited therein.
  • 7
    • 0030749472 scopus 로고    scopus 로고
    • a) K. C. Nicolaou, M. W. Härter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1194
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    • 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.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2821
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    • 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.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 549
  • 12
    • 0344364693 scopus 로고    scopus 로고
    • note
    • 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).
  • 18
    • 0344796503 scopus 로고    scopus 로고
    • note
    • 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.
  • 20
    • 0345659354 scopus 로고    scopus 로고
    • note
    • 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
    • 0345227411 scopus 로고    scopus 로고
    • note
    • Synthetic 1 and 2 exhibited identical chromatographic and spectroscopic data to those of authentic samples.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.