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Volumn 39, Issue 18, 2000, Pages 3315-3319

A combinatorial approach to polyketide-type libraries by iterative asymmetric aldol reactions performed on solid support

Author keywords

[No Author keywords available]

Indexed keywords

POLYKETIDE;

EID: 0034665619     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000915)39:18<3315::AID-ANIE3315>3.0.CO;2-9     Document Type: Article
Times cited : (70)

References (45)
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    • A four-carbon starting aldehyde 9 (n = 2 in 5) was selected initially to demonstrate the viability of the method. This aided characterization by avoiding hemiacetal formation on cleavage of the ketone product from the resin after the first aldol addition. In subsequent work, we have found that the analogous three-carbon aldehyde (n = 1 in 5) is equally reactive to similar enolate reagents. Polystyrene resin (styrene-1% divinylbenzene, 200-400 mesh, Acros) was converted into chlorodiisopropylsilyl polystyrene by the method of Danishefsky et al. J. T. Randolph, K. F. McClure, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5712.
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    • note
    • Our preliminary work was performed with the benzyl instead of the PMB ether in 17 (ref. [3c]), hut this could not be deprotected satisfactorily on the solid support.
  • 40
    • 0342927566 scopus 로고    scopus 로고
    • note
    • 7Na [M + Na] 503.2973; found: 503.2963.
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    • Prepared from methyl (R)-3-hydroxy-2-methylpropionate by analogy with the procedures described previously: a) I. Paterson, R. D. Tillyer, J. Org. Chem. 1993, 58, 4182;
    • (1993) J. Org. Chem. , vol.58 , pp. 4182
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.