메뉴 건너뛰기




Volumn 65, Issue 7, 2000, Pages 2208-2217

Enantioselective total synthesis of (-)-triptolide, (-)-triptonide, (+)- triptophenolide, and (+)-triptoquinonide

Author keywords

[No Author keywords available]

Indexed keywords

TRIPTOLIDE; TRIPTONIDE; TRIPTOPHENOLIDE; TRIPTOQUINONIDE; UNCLASSIFIED DRUG;

EID: 0034616006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9919613     Document Type: Article
Times cited : (88)

References (74)
  • 2
    • 0343172887 scopus 로고
    • Zhong Yi Gu Ji Chu Ban She: Beijing
    • (b) Shen Nong Ben Cao Jing; Huang, S., Ed.; Zhong Yi Gu Ji Chu Ban She: Beijing, 1987.
    • (1987)
    • Jing, S.N.B.C.1    Huang, S.2
  • 34
    • 0342303336 scopus 로고    scopus 로고
    • Triptophenolide methyl ether (5) is also a natural product isolated from TWHf. See ref 3b
    • Triptophenolide methyl ether (5) is also a natural product isolated from TWHf. See ref 3b.
  • 37
    • 0012397313 scopus 로고
    • (a) For a review on ortho-directed metalation, see: Snieckus, V. Chem. Rev. 1990, 90, 879.
    • (1990) Chem. Rev. , vol.90 , pp. 879
    • Snieckus, V.1
  • 41
    • 0342303335 scopus 로고    scopus 로고
    • Manuscript in preparation
    • Yang, D.; Ye, X.-Y. Manuscript in preparation.
    • Yang, D.1    Ye, X.-Y.2
  • 53
    • 22444447467 scopus 로고
    • Wiley: New York, Collect
    • (a) Boehme, W. R. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 590.
    • (1963) Organic Syntheses , vol.4 , pp. 590
    • Boehme, W.R.1
  • 57
    • 0342303333 scopus 로고    scopus 로고
    • note
    • 2) was found to react with the C=C double bond, hence interfering with the chlorination process. Attempts to introduce an a-chloro substituent to β-keto esters by using TfCl/KHMDS produced dichloro compound D as the major product. (equation presented)
  • 58
    • 0027442037 scopus 로고
    • Standard dianion displacement did not give satisfactory yield (ca. 30%). See: Snider, B. B.; McCarthy, B. A. Tetrahedron 1993, 49, 9447.
    • (1993) Tetrahedron , vol.49 , pp. 9447
    • Snider, B.B.1    McCarthy, B.A.2
  • 59
    • 0343608381 scopus 로고    scopus 로고
    • note
    • (b) In our case, the dianion needs to be prepared at -10 to 0°C for 0.5 h in order to achieve high yield (80-87% yield).
  • 60
    • 0343172878 scopus 로고    scopus 로고
    • note
    • Our initial studies on asymmetric radical cyclization involved the use of the following chiral auxiliaries. Compound 17b was cyclized into trans products in poor diastereomer ratio (1.2:1 dr). Amide 17c bearing chiral pyrrolidine auxiliary was cyclized in less than 30% yield. As the cyclization of amides usually affords low chemical yields, the use of chiral amines as auxiliaries in Mn(III)-based oxidative free-radical cyclization becomes extremely limited. (equation presented)
  • 61
    • 0343172876 scopus 로고    scopus 로고
    • note
    • The trans-ring junction products 24 are a mixture of diastereomers, which are inseparable by flash column chromatography. Therefore, the diastereomer ratio was determined after the removal of an a-chloro group.
  • 67
    • 0342303331 scopus 로고    scopus 로고
    • note
    • In the presence of lanthanide triflates, acyclic precursor 17a was decomposed.
  • 74
    • 0342303329 scopus 로고    scopus 로고
    • note
    • The authentic sample of (-)-triptonide (2) was obtained from Shanghai Institute of Materia Medica, Academia Sinica, P. R. China.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.