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Volumn 2, Issue 19, 2000, Pages 3023-3026

Synthetic studies toward phorboxazole A. Stereoselective synthesis of the C28-C46 side chain fragment

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FUSED HETEROCYCLIC RINGS; OXAZOLE DERIVATIVE; PHORBOXAZOLE A; PYRAN DERIVATIVE;

EID: 0034699302     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0063656     Document Type: Article
Times cited : (42)

References (50)
  • 24
    • 0034679493 scopus 로고    scopus 로고
    • (b) Evans, D. A.; Cee, V. J.; Smith, T. E.; Fitch, D. M.; Cho, P. S. Angew. Chem., Int. Ed. 2000, 39, 2533. Evans, D. A.; Fitch, D. M. Angew. Chem., Int. Ed. 2000, 39, 2536.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2536
    • Evans, D.A.1    Fitch, D.M.2
  • 27
    • 0041982462 scopus 로고
    • Alcohol 6 is available from D-glyceraldehyde acetonide via a stereoselective addition of 1-(trimethylsilyl)vinyl copper, followed by protodesilylation. See: (a) Sato, F.; Kusakabe, M. Chem. Lett. 1986, 1473.
    • (1986) Chem. Lett. , vol.1473
    • Sato, F.1    Kusakabe, M.2
  • 29
    • 84982344292 scopus 로고
    • Preparation of stannane 10 is conveniently carried out via deprotonation of 3-methyl-3-buten-1-ol with 2 equiv of Schlosser's base (KOtBu/ "BuLi in hexanes) (see (a) Schlosser, M.; Hartmann, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 508.
    • (1973) Angew. Chem., Int. Ed. Engl. , vol.12 , pp. 508
    • Schlosser, M.1    Hartmann, J.2
  • 30
    • 0041982453 scopus 로고
    • (b) Collum, D. B.; Mguirk, P. R. J. Org. Chem. 1989, 49, 843.) and quenching the resulting dianion with tributyltin iodide. Protection of the resulting primary alcohol with trimethylacetyl chloride/ pyridine provided stannane 10.
    • (1989) J. Org. Chem. , vol.49 , pp. 843
    • Collum, D.B.1    Mguirk, P.R.2
  • 37
    • 85087226461 scopus 로고    scopus 로고
    • note
    • 2 (92%);
  • 38
    • 85087225916 scopus 로고    scopus 로고
    • 3, DBU (81%);
    • 3, DBU (81%);
  • 39
    • 85087228668 scopus 로고    scopus 로고
    • 2 (85%). (equation presented)
    • 2 (85%). (equation presented)
  • 42
    • 0042984009 scopus 로고    scopus 로고
    • note
    • The oxalyl chloride Swern procedure (see ref 12) gave a side product resulting from dichlorination at the C(32) position (72% yield).
  • 43
    • 85087228411 scopus 로고    scopus 로고
    • note
    • 2 (91% yield).
  • 48
    • 0041982457 scopus 로고    scopus 로고
    • note
    • Additionally, small quantities of tetraene 20 have been observed in the Julia olefination reaction resulting from subsequent elimination of methanol. (equation presented)
  • 49
    • 0042483164 scopus 로고    scopus 로고
    • note
    • For example, reaction of sulfone 4 with cinnamaldehyde resulted in an 8:1 ratio of (E,E) to (E,Z) dienes. (equation presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.