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Volumn 68, Issue 11, 2003, Pages 4519-4522

Straightforward synthesis of panaxytriol: An active component of red Ginseng

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; HYDROXYLATION; REDUCTION;

EID: 0038441450     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0341665     Document Type: Article
Times cited : (76)

References (32)
  • 21
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    • note
    • At the present writing, it is not clear to us why the reduction of 2 is significantly more selective than the model cases in ref 9, which bear substitution at the β-carbon of the olefin.
  • 24
    • 0001413313 scopus 로고
    • (a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
    • (1957) Ann. Chim. Paris , vol.2 , pp. 819
    • Chodkiewicz, W.1
  • 25
    • 0004294109 scopus 로고
    • Viehe, H. G., Ed.; Marcel Deker: New York
    • (a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
    • (1969) Chemistry of Acetylenes , pp. 597
    • Chodkiewicz, W.1
  • 26
    • 0004003407 scopus 로고
    • Elsevier, Amsterdam
    • (a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
    • (1988) Preparative Acetylenic Chemistry, 2nd Ed. , pp. 212-214
    • Brandsma, L.1
  • 27
    • 0034604562 scopus 로고    scopus 로고
    • (a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 2632
    • Siemsen, P.1    Livingston, R.C.2    Diederich, F.3
  • 28
    • 0038390570 scopus 로고    scopus 로고
    • note
    • We thank Dr. Yun-Lian Lin, National Research institute of Chinese Medicine, Taipei 112, Taiwan, for sending us a specimen sample of panaxytriol.
  • 29
    • 0038390568 scopus 로고    scopus 로고
    • note
    • 3).
  • 30
    • 0037714457 scopus 로고    scopus 로고
    • note
    • 20 For the absolute configuration of panaxytriol to be opposite to that shown, all of these precedents would have to be inapplicable.
  • 31
    • 0038052256 scopus 로고    scopus 로고
    • note
    • A related Cadiot-Chodkiewicz cross-coupling reaction was reported in the process of total synthesis of panaxytriol (ref 7b). The novelty of our case lies in its application to a setting containing three nonprotected resident hydroxyl groups.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.