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Volumn 133, Issue 19, 2011, Pages 7308-7311

Toward more "ideal" polyketide natural product synthesis: A step-economical synthesis of zincophorin methyl ester

Author keywords

[No Author keywords available]

Indexed keywords

METHYL ESTERS; MULTI-STEP; NATURAL PRODUCT SYNTHESIS; POLYKETIDES; SINGLE-STEP; TAUTOMERIZATIONS;

EID: 79955917868     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201467z     Document Type: Article
Times cited : (54)

References (57)
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    • Discodermolide's journey from discovery to clinical trials has been briefly reviewed. See
    • Discodermolide's journey from discovery to clinical trials has been briefly reviewed. See: Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discovery 2009, 8, 69
    • (2009) Nat. Rev. Drug Discovery , vol.8 , pp. 69
    • Molinski, T.F.1    Dalisay, D.S.2    Lievens, S.L.3    Saludes, J.P.4
  • 13
    • 67649541693 scopus 로고    scopus 로고
    • Synthetic efforts directed toward zincophorin have recently been reviewed. See
    • Synthetic efforts directed toward zincophorin have recently been reviewed. See: Song, Z.; Lohse, A. G.; Hsung, R. P. Nat. Prod. Rep. 2009, 26, 560
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 560
    • Song, Z.1    Lohse, A.G.2    Hsung, R.P.3
  • 24
    • 79955894832 scopus 로고    scopus 로고
    • In all of these syntheses, as well as our own, reagents that had to be synthesized were employed (e.g., 15 in Scheme 3). These syntheses can often be performed once on a large scale, and the reagents are typically reacted with vastly more precious material. Therefore, in a very real sense, these steps have essentially no impact on the overall efficiency of the synthesis. The first number given for total steps does not count these steps, whereas the second number counts every step from commercially available materials.
    • In all of these syntheses, as well as our own, reagents that had to be synthesized were employed (e.g., 15 in Scheme 3). These syntheses can often be performed once on a large scale, and the reagents are typically reacted with vastly more precious material. Therefore, in a very real sense, these steps have essentially no impact on the overall efficiency of the synthesis. The first number given for total steps does not count these steps, whereas the second number counts every step from commercially available materials.
  • 40
    • 79955906666 scopus 로고    scopus 로고
    • The moderate yield of this reaction was due not to the formation of a regioisomer but rather to competitive methylalumination of the alkyne, which led to alkene products that we were unable to supress.
    • The moderate yield of this reaction was due not to the formation of a regioisomer but rather to competitive methylalumination of the alkyne, which led to alkene products that we were unable to supress.
  • 55
    • 33846491932 scopus 로고    scopus 로고
    • Attempts to perform the olefination reaction with a TBS protecting group for the C(19) alcohol were unsuccessful, and this necessitated the switch to a PMB protecting group. The side reactivity of a β-OTBS group on the aldehyde coupling partner in Julia-Kocienski olefination reactions has been explained in detail by Evans. See
    • Attempts to perform the olefination reaction with a TBS protecting group for the C(19) alcohol were unsuccessful, and this necessitated the switch to a PMB protecting group. The side reactivity of a β-OTBS group on the aldehyde coupling partner in Julia-Kocienski olefination reactions has been explained in detail by Evans. See: Evans, D. A.; Nagorny, P.; McRae, K. J.; Sonntag, L.-S.; Reynolds, D. J.; Vounatsos, F. Angew. Chem., Int. Ed. 2007, 46, 545
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 545
    • Evans, D.A.1    Nagorny, P.2    McRae, K.J.3    Sonntag, L.-S.4    Reynolds, D.J.5    Vounatsos, F.6
  • 56
    • 79955916765 scopus 로고    scopus 로고
    • The 43% yield for the conversion of 4 to 5 of course had a large impact on the overall yield. Because this step comes very near the beginning of the sequence, however, the low yield had less of an impact in terms of the loss of valuable material. In that regard, it is worth noting that the overall yield of the 19-step sequence from 5 to 2 was 12%.
    • The 43% yield for the conversion of 4 to 5 of course had a large impact on the overall yield. Because this step comes very near the beginning of the sequence, however, the low yield had less of an impact in terms of the loss of valuable material. In that regard, it is worth noting that the overall yield of the 19-step sequence from 5 to 2 was 12%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.