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Volumn 66, Issue 26, 2010, Pages 4832-4840

The strategic marriage of method and motif. Total synthesis of varitriol

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ETHYLENE OXIDE; NATURAL PRODUCT; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; VARITRIOL; VINYL DERIVATIVE;

EID: 77954243216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.038     Document Type: Article
Times cited : (36)

References (44)
  • 2
    • 64549096370 scopus 로고    scopus 로고
    • For a comparison of this new catalytic method to other dihydrofuran strategies, consult: M. Brichacek, and J.T. Njardarson Org. Biomol. Chem. 7 2009 1761 1770
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 1761-1770
    • Brichacek, M.1    Njardarson, J.T.2
  • 6
    • 77954244226 scopus 로고    scopus 로고
    • Total synthesis of natural (+)-varitriol (1):
    • Total synthesis of natural (+)-varitriol (1):
  • 9
    • 77954242832 scopus 로고    scopus 로고
    • Total synthesis of (-)-varitriol (2):
    • Total synthesis of (-)-varitriol (2):
  • 12
    • 77954244431 scopus 로고    scopus 로고
    • Two studies dedicated to constructing varitriol analogs have been reported in the literature:
    • Two studies dedicated to constructing varitriol analogs have been reported in the literature:
  • 15
    • 77949791510 scopus 로고    scopus 로고
    • An additional chiral approach was published online February 24, 2010. S. Ghosh, and T.K. Pradhap J. Org. Chem. 75 2010 2107 2110
    • (2010) J. Org. Chem. , vol.75 , pp. 2107-2110
    • Ghosh, S.1    Pradhap, T.K.2
  • 16
    • 77954243473 scopus 로고    scopus 로고
    • Although Taylor's synthesis is expedient and beautifully assembles the enantiomer of varitriol (2) it is worth noting that unnatural l-Ribose, which would be needed to access (+)-varitriol (1), is prohibitively expensive and therefore not a suitable chiral starting material.
    • Although Taylor's synthesis is expedient and beautifully assembles the enantiomer of varitriol (2) it is worth noting that unnatural l-Ribose, which would be needed to access (+)-varitriol (1), is prohibitively expensive and therefore not a suitable chiral starting material.
  • 22
    • 77954242305 scopus 로고    scopus 로고
    • In concert with our goal of making the sequence as practical as possible, we have also successfully ring expanded the mixture of epoxides (5/6 and 13/14) obtained from the dienes 4 and 12 to 2,5-dihydrofurans 7 and 15, thus eliminating the need for chromatographically separating the two vinyl oxirane constitutional isomers. These ring expansions have been performed on gram scale.
    • In concert with our goal of making the sequence as practical as possible, we have also successfully ring expanded the mixture of epoxides (5/6 and 13/14) obtained from the dienes 4 and 12 to 2,5-dihydrofurans 7 and 15, thus eliminating the need for chromatographically separating the two vinyl oxirane constitutional isomers. These ring expansions have been performed on gram scale.
  • 24
    • 77954242197 scopus 로고    scopus 로고
    • For similar Darzen reaction examples employing a bromo acrylate and acrolein derivatives to access vinyl oxiranes like 20, see:
    • For similar Darzen reaction examples employing a bromo acrylate and acrolein derivatives to access vinyl oxiranes like 20, see:
  • 27
    • 77954243801 scopus 로고    scopus 로고
    • By using an acyl pyrrole variant of 17 instead of a t-butyl ester an asymmetric variant of 20 could be accessed following Shibasaki's impressive epoxidation protocol.
    • By using an acyl pyrrole variant of 17 instead of a t-butyl ester an asymmetric variant of 20 could be accessed following Shibasaki's impressive epoxidation protocol.
  • 30
    • 58149151106 scopus 로고    scopus 로고
    • Interestingly, the equivalent aziridine substrate of 19 does successfully ring expand M. Brichacek, D. Lee, and J.T. Njardarson Org. Lett. 10 2008 5023 5026 We attribute this difference to the fact that the aziridine nitrogen atom coordinates more effectively to the copper catalyst than the oxirane oxygen atom and the competing hydride shift pathway the vinyl oxirane substrates need to overcome, while the aziridines do not
    • (2008) Org. Lett. , vol.10 , pp. 5023-5026
    • Brichacek, M.1    Lee, D.2    Njardarson, J.T.3
  • 31
    • 77954244575 scopus 로고    scopus 로고
    • 3
    • 3
  • 32
    • 77954243998 scopus 로고    scopus 로고
    • This product could be used to access varitriol analogs.
    • This product could be used to access varitriol analogs.
  • 34
    • 0347090287 scopus 로고    scopus 로고
    • We have been able to find only one example in the literature, wherein an acrylate group is exchanged for a terminal olefin. This was accomplished in modest yields using Grubbs second generation catalyst and ethylene: M.G. Banwell, and D.T.J. Loong Heterocycles 62 2004 713 734
    • (2004) Heterocycles , vol.62 , pp. 713-734
    • Banwell, M.G.1    Loong, D.T.J.2
  • 38
    • 0037463034 scopus 로고    scopus 로고
    • We also considered epoxidizing the known (E,E)-diene homoallylic alcohol using Yamamoto's new asymmetric epoxidation protocol: N. Makita, Y. Hoshino, and H. Yamamoto Angew. Chem., Int. Ed. 42 2003 941 943
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 941-943
    • Makita, N.1    Hoshino, Y.2    Yamamoto, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.