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Volumn 4, Issue 15, 2002, Pages 2473-2476

Toward the combinatorial synthesis of polyketide libraries: Asymmetric aldol reactions with α-chiral aldehydes on solid support

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; 6 DEOXYERYTHRONOLIDE B; 6-DEOXYERYTHRONOLIDE B; ACETAL DERIVATIVE; ALDEHYDE; ALDOL; ALKANE; CARBAMIC ACID DERIVATIVE; DISCODERMOLIDE; DRUG DERIVATIVE; ERYTHROMYCIN; KETONE; LACTONE; POLYMER; PYRONE DERIVATIVE;

EID: 0012407101     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026046+     Document Type: Article
Times cited : (48)

References (44)
  • 11
    • 0030590403 scopus 로고    scopus 로고
    • For other approaches to solid-phase polyketide synthesis, see: (a) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6851
    • Reggelin, M.1    Brenig, V.2
  • 21
    • 0001436716 scopus 로고    scopus 로고
    • (c) Katz, L. Chem. Rev. 1997, 97, 2557.
    • (1997) Chem. Rev. , vol.97 , pp. 2557
    • Katz, L.1
  • 28
    • 84872261269 scopus 로고    scopus 로고
    • note
    • It was not possible to attach alcohol 9 directly to the chlorodiisopropylsilylpolystyrene resin used in our earlier work (ref 3e), necessitating the introduction of this new silyl linker protocol.
  • 29
    • 84872266808 scopus 로고    scopus 로고
    • note
    • The hydroxy-modified Merrifield resin (1% DVB, 100-200 mesh) was purchased from Novabiochem and used without further manipulation.
  • 34
    • 84872265363 scopus 로고    scopus 로고
    • note
    • Attempts to determine the yield and the diastereoselectivity at this stage by cleavage of the resin with HF·pyr/pyr gave only complex mixtures due to hemiacetal formation with the ketone group.
  • 40
    • 84872274750 scopus 로고    scopus 로고
    • note
    • 2BOTf) to promote Z-enolization and syn-aldol additions of ketone (S)-4 s led only to poor yields and stereoselectivities with resin-bound aldehyde 3.
  • 43
    • 84872271596 scopus 로고    scopus 로고
    • note
    • 4, catecholborane, DIBAL) gave lower or overturned selectivities.
  • 44
    • 84872273072 scopus 로고    scopus 로고
    • note
    • After TBAF cleavage of resin 27, triol 28 was isolated in 30% yield over four steps.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.