메뉴 건너뛰기




Volumn , Issue 9 SPEC. ISS., 2003, Pages 1307-1310

A stereoselective approach to the core structure of the polyoxin and nikkomycin antibiotics

Author keywords

Amino acids; Antifungal agents; Carbohydrates; Diastereoselectivity; Stereoselective synthesis

Indexed keywords

ANTIBIOTIC AGENT; NIKKOMYCIN Z; POLYOXIN C; POLYOXIN L; UNCLASSIFIED DRUG;

EID: 0037765590     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40341     Document Type: Article
Times cited : (21)

References (48)
  • 32
    • 0038585939 scopus 로고    scopus 로고
    • note
    • (a) Early studies involved the use of uridine as a starting material, with the intention of utilizing an asymmetric Ugi condensation or an asymmetric Strecker reaction as the key operation. Unfortunately, the required imine derivatives were either unstable or resulted in poor selectivity upon nucleophilic addition. In the ribose series, the key stereocenter could be formed using a chiral auxiliary-mediated Strecker reaction, but the resulting amino-nitrile could not be hydrolyzed.
  • 41
    • 0038585933 scopus 로고    scopus 로고
    • note
    • Attempted use of the zinc acetylide addition with a uridine-derived aldehyde was thwarted by a complete lack of reactivity with a variety of alkynes.
  • 42
    • 84981848681 scopus 로고
    • Alcohol 2 was prepared on a 30-gram scale in 79% yield by a modification of the procedure found in: Leonard, N. J.; Carraway, K. L. J. Heterocycl. Chem. 1966, 3, 485.
    • (1966) J. Heterocycl. Chem. , vol.3 , pp. 485
    • Leonard, N.J.1    Carraway, K.L.2
  • 44
    • 0037571667 scopus 로고    scopus 로고
    • note
    • 3/pyridine, TPAP, IBX/DMSO, Dess-Martin) proved to be much less reliable for this transformation, being difficult to reproduce and providing aldehyde of lower purity than with IBX.
  • 45
    • 0038247315 scopus 로고    scopus 로고
    • note
    • 5N 322.1654, found 322.1657.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.