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Volumn 7, Issue 17, 2005, Pages 3617-3620

Synthesis of the aglycones of altromycins and kidamycin from a common intermediate

Author keywords

[No Author keywords available]

Indexed keywords

ALTROMYCIN A; AMINOGLYCOSIDE; ANTINEOPLASTIC ANTIBIOTIC; KIDAMYCIN;

EID: 24044456667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0509742     Document Type: Article
Times cited : (43)

References (39)
  • 14
    • 24044536953 scopus 로고    scopus 로고
    • For another synthesis of the altromycin branched C-glycoside substructure, see the following communication: Koo, B.; McDonald, F. E. Org. Lett. 2005, 7, 3621.
    • (2005) Org. Lett. , vol.7 , pp. 3621
    • Koo, B.1    McDonald, F.E.2
  • 21
    • 0023831584 scopus 로고
    • For similar examples of this addition - elimination reaction, see: (a) Hormi, O. E. O. J. Org. Chem. 1988, 53, 880.
    • (1988) J. Org. Chem. , vol.53 , pp. 880
    • Hormi, O.E.O.1
  • 23
  • 27
    • 33645604999 scopus 로고    scopus 로고
    • note
    • Attempted isomerization of 16 to the conjugated isomer 15 was unsuccessful under acidic or basic conditions.
  • 30
    • 33645589905 scopus 로고    scopus 로고
    • note
    • As the absolute stereochemistry of the C14-C16 epoxide of altromycin has not been established, it is desirable to synthesize both epoxide enantiomers of 1. Thus, treatment of 19 with AD-mix-α under the same conditions produced ent-20 (12:1 er), which was converted into ent-1.
  • 32
    • 33645597814 scopus 로고    scopus 로고
    • note
    • (b) The use of ethanethiol (ref 17a) resulted in ethanethiol substitution at Cl2 as the sole product, but the more bulky tert-butanethiol was successfully applied to give only 21.
  • 33
    • 33645595574 scopus 로고    scopus 로고
    • note
    • Tris-TIPS-protected intermediate was unstable and air oxidized to tris-TIPS-protected quinone during attempted product isolation.
  • 36
    • 33645583484 scopus 로고    scopus 로고
    • see Supporting Information
    • Structure assignment was determined by NOE analysis of compound 25 (see Supporting Information).
  • 38
    • 33645601946 scopus 로고    scopus 로고
    • note
    • Use of methylmagnesium bromide occasionally resulted in significant amounts of a byproduct from conjugate addition of methyl Grignard to the C16-C14 alkene under extended reaction times.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.