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Volumn 43, Issue 34, 2004, Pages 4523-4526

Total synthesis of xerulinic acid

Author keywords

C C coupling; Inhibitors; Lactones; Natural products; Stereoselective synthesis

Indexed keywords

BIOSYNTHESIS; CATALYSIS; CHOLESTEROL; ESTERS; PALLADIUM;

EID: 4544296929     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453729     Document Type: Article
Times cited : (52)

References (50)
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    • For reviews, see: a) J. K. Stille, Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 508-524
  • 17
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    • note
    • 13CNMR spectra and correct elemental analyses, except acid 12, unstable ester 4 a, and xerulinic acid (3), for all of which, however, correct high-resolution mass spectra were obtained.
  • 21
    • 0024232887 scopus 로고
    • Prepared by a procedure analogous to that of: a) N. Jeker, C. Tamm, Helv. Chim. Acta 1988, 71, 1895-1903;
    • (1988) Helv. Chim. Acta , vol.71 , pp. 1895-1903
    • Jeker, N.1    Tamm, C.2
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    • Ph.D. thesis, Universität Freiburg
    • Method: F. Reimnitz, Ph.D. thesis, Universität Freiburg, 2000, pp. 71-72, 147-148.
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    • Reimnitz, F.1
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    • The method is same as that described for the oxidation of heterocycle-substituted sulfides en route to Julia-Lythgoe olefins: P. A. Blakemore, P. J. Kocienski, S. Marzcak, J. Wicha, Synthesis 1999, 1209-1215.
    • (1999) Synthesis , pp. 1209-1215
    • Blakemore, P.A.1    Kocienski, P.J.2    Marzcak, S.3    Wicha, J.4
  • 29
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    • note
    • 2 (656.3): C 54.74, H 9.19; found: C53.81, H 8.97.
  • 35
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    • a) A. Kiehl, A. Eberhardt, M. Adam, V. Enkelmann, K. Müllen, Angew. Chem. 1992, 104, 1623-1626; Angew. Chem. Int. Ed. Engl. 1992, 31, 1588-1591;
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    • 10-bis(tributylstannane) has also been synthesized and used as a building block: B. Vaz, R. Alvarez, A. R. de Lera, J. Org. Chem. 2002, 67, 5040-5043.
    • (2002) J. Org. Chem. , vol.67 , pp. 5040-5043
    • Vaz, B.1    Alvarez, R.2    De Lera, A.R.3
  • 39
    • 4544222996 scopus 로고    scopus 로고
    • note
    • The aforementioned authors prepared lactone 6 for the first time but the Experimental Section of their study details no more than a 2% yield of 6 separated chromatographically from a 54%:8%:3%:2%:trace mixture of five compounds; accordingly, 6 becomes a synthetically useful reagent only on the grounds of our two-step synthesis (Scheme 5).
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    • Kumar, N.1    Read, R.W.2
  • 41
    • 4544364647 scopus 로고    scopus 로고
    • note
    • 2 (174.4): C 34.32, H 1.73; found: C 34.20, H 1.61.
  • 42
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    • For reviews, see: a) E. Erdik, Tetrahedron 1992, 48, 9577-9648;
    • (1992) Tetrahedron , vol.48 , pp. 9577-9648
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    • (Edk: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • c) P. Knochel in Metal-catalyzed Cross-coupling Reactions (Edk: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 387-416.
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  • 48
    • 4544368603 scopus 로고    scopus 로고
    • note
    • 4Si (392.1): C 70.38, H 6.16; found: G 70.15, H 6.13.
  • 49
    • 4544328578 scopus 로고    scopus 로고
    • personal communication
    • W. Steglich, personal communication. We are indebted to Professor Steglich for sending copies of all the original NMR spectra of compound 3.
    • Steglich, W.1
  • 50
    • 4544222164 scopus 로고    scopus 로고
    • Ph.D. Thesis, Universität Freiburg
    • A referee suggested that "the possibility of directly obtaining xerulinic acid from xerulin should be commented on". We are unaware of such a possibility; furthermore, during alternative attempts at the synthesis of xerulinic acid, we prepared both the corresponding alcohol (" xerulinol") and aldehyde ("xerulinal") but could not oxidize either to xerulinic acid: K. Siegel, Ph.D. Thesis, Universität Freiburg, 2000.
    • (2000)
    • Siegel, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.