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Volumn 3, Issue 5, 2001, Pages 707-710

Total synthesis of the immunosupressant (-)-pironetin (PA48153C)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IMMUNOSUPPRESSIVE AGENT; PIRONETIN; PYRONE DERIVATIVE;

EID: 0035826353     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015531m     Document Type: Article
Times cited : (61)

References (31)
  • 1
    • 0024955297 scopus 로고
    • For general reviews, see: (a) Borel, J. F. Pharmacol. Rev. 1990, 41, 259.
    • (1990) Pharmacol. Rev. , vol.41 , pp. 259
    • Borel, J.F.1
  • 10
    • 0041906337 scopus 로고    scopus 로고
    • European Patent 60389 Al, 1993
    • (b) European Patent 60389 Al, 1993.
  • 24
    • 0041405219 scopus 로고    scopus 로고
    • note
    • It was straightforward to prepare the corresponding benzyl ether by using the Evans oxazolidinone alkylation procedure with chloromethylbenzyl ether as the alkylating agent, and the derived β-benzyloxy methyl ketone intermediate was used sucessfully in condensation with aldehyde 6. However, all attempts to remove the benzyl ether at the stage of intermediate 21 were either compromised by olefin reduction or by acetate migration. Also, it proved impractical to prepare the p-methoxybenzyl ether 18 using the simple sequence employed to prepare the corresponding benzyl ether.
  • 28
    • 0041906334 scopus 로고    scopus 로고
    • note
    • β and the aldehyde oxygen, while interchanging H and the O substituent will give both a diaxial steric interaction and also maximum dipole-dipole repulsion between the two C-O bonds. Although there might be some ambiguity about which of these alternative arrangements would be favored, it is a certainty that both would be considerably higher in energy than the preferred arrangement depicted.
  • 30
    • 0041405218 scopus 로고    scopus 로고
    • note
    • A similar level of stereoselectivity was obtained using tetramethylammonium triacetoxyborohydride reduction. In contrast, both reductions were completely stereoselective for the anti diol when conducted on the corresponding benzyl compound (19 with PMB replaced by benzyl).
  • 31
    • 0042407570 scopus 로고    scopus 로고
    • note
    • The spectral and analytical data for 1 were in excellent agreement with that previously reported for the natural material and that from previous synthetic efforts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.