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Volumn 38, Issue 11, 1999, Pages 1669-1675

Total synthesis of the CP molecules CP-263,114 and CP-225,917- Part 1: Synthesis of key intermediates and intelligence gathering

Author keywords

Domino reactions; Natural products; Polycycles; Total synthesis

Indexed keywords

CP 225917; CP 263114; FARNESYL TRANS TRANSFERASE; HYPOCHOLESTEROLEMIC AGENT; SQUALENE SYNTHETASE; UNCLASSIFIED DRUG;

EID: 0033153049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1669::AID-ANIE1669>3.0.CO;2-D     Document Type: Article
Times cited : (111)

References (48)
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    • For this methodology, see reference [4a]
    • For this methodology, see reference [4a].
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    • For this methodology, see reference [41]
    • For this methodology, see reference [41].
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    • Prepared in two steps from cyclooctene using Schreiber's terminally differentiating ozonolysis protocol (R. E. Claus, S. L. Schreiber, Org. Synth. 1986, 64, 150) followed by a Schlosser modified (M. Schlosser, K. F. Christmann, Liebigs Ann. 1967, 708, 1) Wittig reaction and workup with TsOH to remove the dimethyl acetal.
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    • Prepared in two steps from cyclooctene using Schreiber's terminally differentiating ozonolysis protocol (R. E. Claus, S. L. Schreiber, Org. Synth. 1986, 64, 150) followed by a Schlosser modified (M. Schlosser, K. F. Christmann, Liebigs Ann. 1967, 708, 1) Wittig reaction and workup with TsOH to remove the dimethyl acetal.
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    • note
    • The attempted oxidation failed even in substrates that did not contain the maleic anhydride moiety.
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    • To the best of our knowledge this is the first time an acyl mesylate has been used to synthesize a diazoketone. Although conditions have been reported for the formation of acyl mesylates, they are quite harsh (heat in benzene; see Z. M. Jászay, I. Petneházy, L. Töke, Synthesis 1989, 745). The present conditions have never failed in our hands so far when used with a variety of different sterically congested carboxylic acids.
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    • note
    • The use of ester groups (-OMe, -OTPS, O-tBu) at C-29 led to rapid cyclization to form γ-lactones upon release of the neighboring diol.
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    • note
    • Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as Supplementary publication no. CCDC-118962. Copies of the data can be obtained free of charge on application to CCDC, 12 Union road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033: e-mail: deposit@ccc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.