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Volumn 122, Issue 38, 2000, Pages 9099-9108

Total synthesis of thyrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and an anti-leukemic inducer of apoptosis

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ANTILEUKEMIC AGENT; CHROMIUM DERIVATIVE; DEXTRO GLUTAMIC ACID; EPOXIDE; GERANIOL; NATURAL PRODUCT; ORGANOMETALLIC COMPOUND; PHOSPHOPROTEIN PHOSPHATASE 2A; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; TETRAHYDROPYRAN DERIVATIVE; THYRSIFEROL; THYRSIFERYL 18 ACETATE; THYRSIFERYL 18,23 DIACETATE; THYRSIFERYL 23 ACETATE; UNCLASSIFIED DRUG;

EID: 0039333274     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000001r     Document Type: Article
Times cited : (78)

References (96)
  • 11
    • 0342733238 scopus 로고    scopus 로고
    • note
    • Thyrsiferol (1b), 15(28)-anhydrothyrsiferyl-23-acetate (2a), thyrsiferyl 18-acetate (1c), and thyrsiferyl 15, 18, 23-triacetate.
  • 18
    • 0023691731 scopus 로고
    • 50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
    • (1988) Biochem. J. , vol.256 , pp. 283-290
    • Bialojan, C.1    Takai, A.2
  • 20
    • 0030720062 scopus 로고    scopus 로고
    • 50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
    • (1997) FEBS Lett. , vol.416 , pp. 230-234
    • Walsh, A.H.1    Cheng, A.2    Honkanen, R.E.3
  • 25
    • 0343167748 scopus 로고    scopus 로고
    • note
    • 50 1c = 464 nM. 2
  • 47
    • 0343603167 scopus 로고    scopus 로고
    • note
    • This approximate yield was obtained after purification of the crude mixture through a short silica gel column; further purification using MPLC caused loss of material.
  • 48
    • 0343167746 scopus 로고    scopus 로고
    • note
    • The ratio was determined by GC using a DBS column (10m × 0.1 mm × 0.1 μm film thickness).
  • 63
    • 0342733230 scopus 로고    scopus 로고
    • note
    • The corresponding cis epoxides have been shown to disfavor the 6-endo mode of ring closure.
  • 72
    • 0342733226 scopus 로고    scopus 로고
    • note
    • For a precedent of this reaction in a cis dibromoalkenyl epoxide, see ref 35.
  • 82
    • 0342298251 scopus 로고    scopus 로고
    • note
    • The stereochemistry of tetrahydrofurans 40 was determined at the stage of the diacetate derivatives. The diacetate 46, derived from 40a, showed an NOE between protons al the C18 and C22 positions (Scheme 8).
  • 84
    • 0343603157 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the trans-tetrahydrofuran 41a was determined after protecting the two free hydroxyls with MOM groups, by detection of an NOE between protons at the C18 and C22 positions.
  • 92
    • 0342733225 scopus 로고    scopus 로고
    • note
    • 1H NMR determination of the crude mixture it was possible to distinguish the two possible isomers in the ratio 3:1; however, the stereochemistry at the C15 was not assigned.
  • 96
    • 0342298250 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of semisynthetic 1c obtained from a natural sample of 1b, which was kindly provided by Prof. J. W. Blunt.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.