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Volumn 37, Issue 7, 1996, Pages 1081-1084

Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; SIPHONARIENONE; UNCLASSIFIED DRUG;

EID: 0030041259     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02353-4     Document Type: Article
Times cited : (60)

References (13)
  • 3
    • 33751158743 scopus 로고
    • Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. J. Am. Chem. Soc. 1990, 112, 5290. White, D. J.; Johnson, A. T. J. Org. Chem. 1994, 59, 3347.
    • (1994) J. Org. Chem. , vol.59 , pp. 3347
    • White, D.J.1    Johnson, A.T.2
  • 5
    • 85030190343 scopus 로고    scopus 로고
    • note
    • (S)-2 was prepared in multi-gram quantity by resolution of (±)-2-methylpentanoic acid with the (-)-isoxazolidine, followed by reduction. (equation presented)
  • 6
    • 85030187148 scopus 로고    scopus 로고
    • note
    • After warming an enolate solution (-78∼-30 °C, 1 h), 1 was recovered in 75 % yield along with fragmentation products, from which 20 was isolated. (equation presented)
  • 10
    • 0039704156 scopus 로고
    • 10 was converted to the corresponding known diol: Chiarello, J.; Joullie. M. M. Synth. Commun. 1989, 19, 3379. ent-12: Tsuda, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1994, 59, 3734.
    • (1989) Synth. Commun. , vol.19 , pp. 3379
    • Chiarello, J.1    Joullie, M.M.2
  • 11
    • 0028147182 scopus 로고
    • 10 was converted to the corresponding known diol: Chiarello, J.; Joullie. M. M. Synth. Commun. 1989, 19, 3379. ent-12: Tsuda, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1994, 59, 3734.
    • (1994) J. Org. Chem. , vol.59 , pp. 3734
    • Tsuda, M.1    Sasaki, T.2    Kobayashi, J.3
  • 12
    • 85030188672 scopus 로고    scopus 로고
    • note
    • The triflate of anti-alcohol 15 was prepared in diethyl ether at -78 °C and 2.5 eq. of the enolate solution in diethyl ether was transferred via cannula.
  • 13
    • 85030190770 scopus 로고    scopus 로고
    • note
    • 13C NMR δ 69.0, 68.0, 41.4, 40.6, 33.0, 32.9, 27.2, 20.3, 17.2, 16.5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.