메뉴 건너뛰기




Volumn 38, Issue 39, 1997, Pages 6825-6828

Total synthesis of rhizoxin D

Author keywords

[No Author keywords available]

Indexed keywords

RHIZOXIN; RHIZOXIN D; UNCLASSIFIED DRUG;

EID: 0030839481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01605-5     Document Type: Article
Times cited : (37)

References (36)
  • 5
    • 0343448543 scopus 로고    scopus 로고
    • ORGN (New Orleans)
    • Although the rhizoxin diene 2 was not named by investigators responsible for its discovery (ref. 2a), we have referred to this natural product as rhizoxin D. An account of our total synthesis was previously presented: Williams, D.R.; Werner, K.M.; Feng, B. National Meeting; American Chemical Society, 1996, 211th, ORGN 442 (New Orleans).
    • (1996) National Meeting; American Chemical Society , vol.211 TH , pp. 442
    • Williams, D.R.1    Werner, K.M.2    Feng, B.3
  • 29
    • 0025058974 scopus 로고
    • 13C-NMR data for the pair of acetonides individually characterized from desilylation of 16 See: Rychnovsky, S.D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 945
    • Rychnovsky, S.D.1    Skalitzky, D.J.2
  • 31
    • 33845282438 scopus 로고
    • Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen, C.-P.; Singh, V.K. J. Am. Chem. Soc. 1987, 109, 7925. Mathre, D.J.; Jones, T.K.; Xavier, L.C.; Blacklock, T.J.; Reamer, R.A.; Mohan, J.J.; Jones, E.T.T.; Hoogsteen, K.; Baum, M.W.; Grabowski, E.J.J. J. Org. Chem. 1991, 56, 751.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7925
    • Corey, E.J.1    Bakshi, R.K.2    Shibata, S.3    Chen, C.-P.4    Singh, V.K.5
  • 33
    • 0343870882 scopus 로고    scopus 로고
    • note
    • 7 alcohol resulting only from removal of the THP ether. However, longer reaction times or increased temperatures led to numerous side products.
  • 34
    • 0025143164 scopus 로고
    • and references therein
    • For an example: Williams, D.R.; McGill, J.M. J. Org. Chem. 1990, 55, 3457, and references therein.
    • (1990) J. Org. Chem. , vol.55 , pp. 3457
    • Williams, D.R.1    McGill, J.M.2
  • 36
    • 0022457825 scopus 로고
    • In practice, our Wittig reactions led to crude product with some hydrolytic opening of the valerolactone. Submission to Yamaguchi conditions (procedure: Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221) recovered this material prior to purification.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 5221
    • Suzuki, K.1    Tomooka, K.2    Katayama, E.3    Matsumoto, T.4    Tsuchihashi, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.