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Volumn 43, Issue 44, 2004, Pages 5991-5994

Enantioselective total synthesis of the highly oxygenated 1,10-seco-eudesmanolides eriolanin and eriolangin

Author keywords

Domino reactions; Natural products; Sulfur heterocycles; Terpenoids; Total synthesis

Indexed keywords

ACTIVATION ANALYSIS; ADDITION REACTIONS; BIOMATERIALS; MOLECULAR ORIENTATION; SYNTHESIS (CHEMICAL);

EID: 9244236524     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460936     Document Type: Article
Times cited : (35)

References (46)
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    • Review on sultone chemistry: P. Metz, J. Prakt. Chem. 1998, 340, 1-10.
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    • US 6,627,623 B2, 2003
    • Compounds 3 and 4 effect phosphorylation of the antiapoptosis protein Bcl-2 and induce apoptosis in several cancer cell lines; for 4 cell-cycle arrest at the G2/M phase as well as polymerization of microtubules was proven: C.-T. Ho, M. Rafi, R. S. Dipaola, G. Ghai, R. T. Rosen, N. Bai, US 6,627,623 B2, 2003.
    • Ho, C.-T.1    Rafi, M.2    Dipaola, R.S.3    Ghai, G.4    Rosen, R.T.5    Bai, N.6
  • 9
    • 0037359287 scopus 로고    scopus 로고
    • For the relative configuration of 3 and 4 shown in Scheme 1, see ref. [5b] as well as the crystal structures of 3 depicted in: a) A.-R. Han, W. Mar, E.-K. Seo, Nat. Prod. Sci. 2003, 9, 28-30;
    • (2003) Nat. Prod. Sci. , vol.9 , pp. 28-30
    • Han, A.-R.1    Mar, W.2    Seo, E.-K.3
  • 12
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    • P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 1994, 106, 2275-2276; Angew. Chem. Int. Ed. Engl. 1994, 33, 2195-2197.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2195-2197
  • 16
    • 0000374349 scopus 로고
    • This unusual regioselectivity of epoxide opening was already reported for racemic 8: B. Alcaide, P. Areces, E. Borredon, C. Biurrun, J. P. Castells, J. Plumet, Heterocycles 1990, 31, 1997-2002. We found that the stereochemical course is strongly dependent on the nature of the methyl nucleophile. With methylmagnesium bromide, again regioisomer 9 is preferentially formed; however, the reaction proceeds with extensive racemization.
    • (1990) Heterocycles , vol.31 , pp. 1997-2002
    • Alcaide, B.1    Areces, P.2    Borredon, E.3    Biurrun, C.4    Castells, J.P.5    Plumet, J.6
  • 27
    • 9244226236 scopus 로고    scopus 로고
    • note
    • Apparently the intermediate allylcarbenium ion is trapped by the solvent DMF as the nucleophile to generate an immonium ion, which is converted to the formate during aqueous workup.
  • 31
    • 9244223865 scopus 로고    scopus 로고
    • note
    • Experiments toward Mitsunobu inversion at C6 in 24 were not successful.
  • 32
    • 9244255025 scopus 로고    scopus 로고
    • note
    • Increasing the reaction temperature in order to achieve complete reduction caused desilylation of the secondary silyl ether.
  • 37
    • 9244231521 scopus 로고    scopus 로고
    • note
    • In addition to 27 the C6-epimeric alcohol was isolated in 6% yield.
  • 40
    • 9244255024 scopus 로고    scopus 로고
    • note
    • b) Addition of molecular sieves 4 Å in the first step caused a significant increase in yield.
  • 43
    • 9244245499 scopus 로고    scopus 로고
    • note
    • 3).
  • 44
    • 9244238960 scopus 로고    scopus 로고
    • -3, Flack parameter 0.04(19). Programs used: EXPRESS, MolEN, SHELXS-97, SHELXL-97, SCHAKAL. CCDC-239240 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 46
    • 9244237292 scopus 로고    scopus 로고
    • note
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.