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Volumn , Issue 21, 2009, Pages 3694-3707

Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

Author keywords

Asymmetric catalysis; Enantioselective synthesis; Nozaki Hiyama reaction; Structure elucidation; Total synthesis

Indexed keywords

ASYMMETRIC CATALYSIS; AVERAGE YIELD; ENANTIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; HMG-COA REDUCTASE INHIBITOR; REACTION STRUCTURES; STATINS; STRUCTURE ELUCIDATION; TOTAL SYNTHESIS;

EID: 72049101650     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/S-0029-1216980     Document Type: Review
Times cited : (2)

References (36)
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    • 2nd ed.; Gaw, A.; Packard, C. J.; Shepherd, J., Eds.; Martin Dunitz: London
    • (c) Statins: The HMG CoA Reductase Inhibitors in Perspective, 2nd ed.; Gaw, A.; Packard, C. J.; Shepherd, J., Eds.; Martin Dunitz: London, 2004.
    • (2004) Statins: the HMG CoA Reductase Inhibitors in Perspective
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    • 0023038220 scopus 로고
    • For a recent total synthesis of (+)-dihydrocompactin, see
    • To the best of our knowledge, 1 and 2 are the first naturally occurring statins found to possess a tetralin core. Total syntheses of statins incorporating a hexalin core or an octalin core have been reported. For an early review, see: (a) Rosen, T.; Heathcock, C. H. Tetrahedron 1986, 42, 4909. For a recent total synthesis of (+)-dihydrocompactin, see:
    • (1986) Tetrahedron , vol.42 , pp. 4909
    • Rosen, T.1    Heathcock, C.H.2
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    • 72049102042 scopus 로고    scopus 로고
    • The use of ent-12 afforded ent-34 accordingly
    • The use of ent-12 afforded ent-34 accordingly.
  • 29
    • 72049117552 scopus 로고    scopus 로고
    • CCDC 647745 contains the supplementary crystallographic data (excluding structure factors) for this paper. These data can be obtained free of charge from. The Cambridge Crystallographic Data Centre via
    • CCDC 647745 contains the supplementary crystallographic data (excluding structure factors) for this paper. These data can be obtained free of charge from. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
  • 34
    • 0034725917 scopus 로고    scopus 로고
    • For the precedent synthesis of the β-hydroxy-5-lactone moiety, see: Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779.
    • (2000) Org. Chem. , vol.65 , pp. 4779
    • Ghosh, A.K.1    Lei, H.J.2
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    • 23 -16 (c 0.40, MeOH)}. However, we soon found out that this difference was due to the methanolysis of 2 during the measurement of the specific rotation. That is, δ-lactone 2 was converted into the methyl ester of 1 by its reaction with MeOH, which was used as the solvent
    • 23 -16 (c 0.40, MeOH)}. However, we soon found out that this difference was due to the methanolysis of 2 during the measurement of the specific rotation. That is, δ-lactone 2 was converted into the methyl ester of 1 by its reaction with MeOH, which was used as the solvent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.