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Volumn , Issue 22, 2006, Pages 2388-2390

Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: A formal synthesis

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; KENDOMYCIN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYKETIDE; UNCLASSIFIED DRUG;

EID: 33744939244     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b602937j     Document Type: Article
Times cited : (48)

References (58)
  • 6
    • 33744933545 scopus 로고    scopus 로고
    • 239489
    • Chem. Abs., 1998, 128, 239489
    • (1998) Chem. Abs.
  • 51
    • 33744932026 scopus 로고    scopus 로고
    • note
    • The syn stereochemistry and the olefin geometry govern the configurations of the tetrahydropyranyl substituents upon cyclization through a chair-like transition state with an (E)-oxocarbenium ion
  • 54
    • 0021830019 scopus 로고
    • Reported in the supplementary information are detailed and optimized experimental procedures for the economic, half-mole scale throughput of the precursors to Kubo's hydroxybenzaldehyde from commercially available 2,6-dimethoxytoluene Replacement of the electron-withdrawing acetate or sulfonate groups with methyl resulted mostly in fragmentation products, with only 20% yield of the desired C-aryl glycoside. The problematic role of electron-rich aromatic rings has been previously reported. See ref. 9b This alcohol, (E,4R,5R,8S)-4,8-dimethyldeca-2,9-dien-5-ol, was prepared by allylation of the known aldehyde, (4S)-methyl-hex-5-enal
    • A. Kubo Y. Kitahara S. Nakahara R. Numata Chem. Pharm. Bull. 1985 33 2122
    • (1985) Chem. Pharm. Bull. , vol.33 , pp. 2122
    • Kubo, A.1    Kitahara, Y.2    Nakahara, S.3    Numata, R.4
  • 56
    • 33744944639 scopus 로고    scopus 로고
    • Propylene oxide was used as an acid scavenger in the bromination reaction to avoid loss of the phenolic TBS group
    • Propylene oxide was used as an acid scavenger in the bromination reaction to avoid loss of the phenolic TBS group


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.