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Volumn 10, Issue 11, 2008, Pages 2115-2118

Stereocontrolled synthesis of the sterically encumbered F ring of lancifodilactone G

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EID: 59849102394     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800419v     Document Type: Article
Times cited : (35)

References (31)
  • 1
    • 51549107852 scopus 로고    scopus 로고
    • For our preliminary results on synthesis of ABC fragment of lancifodilactone G, see
    • For our preliminary results on synthesis of ABC fragment of lancifodilactone G, see: Paquette, L. A.; Lai, K. W. Org. Lett. 2008, 10, 2111-2114.
    • (2008) Org. Lett , vol.10 , pp. 2111-2114
    • Paquette, L.A.1    Lai, K.W.2
  • 3
    • 30744465911 scopus 로고    scopus 로고
    • For a review of anomeric effects in natural product synthesis, see
    • For a review of anomeric effects in natural product synthesis, see: Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406.
    • (2005) Chem. Rev , vol.105 , pp. 4406
    • Aho, J.E.1    Pihko, P.M.2    Rissa, T.K.3
  • 4
    • 0023149444 scopus 로고
    • For an early application of stereochemically linear strategy, see
    • For an early application of stereochemically linear strategy, see: Smith, A. B., III; Fukui, M. J. Am. Chem. Soc. 1987, 109, 1269.
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 1269
    • Smith III, A.B.1    Fukui, M.2
  • 7
    • 59849128261 scopus 로고    scopus 로고
    • The carbon numbering is accorded to the system of the parent natural product in ref 2
    • The carbon numbering is accorded to the system of the parent natural product in ref 2.
  • 14
    • 59849097192 scopus 로고    scopus 로고
    • The stereochemical outcome was not determined. The major isomer was separated by column chromatography and was used for the subsequent reduction reaction
    • The stereochemical outcome was not determined. The major isomer was separated by column chromatography and was used for the subsequent reduction reaction.
  • 19
    • 0034644383 scopus 로고    scopus 로고
    • For precedent speculation regarding the formation of mixed tert-butylalkylzinc species in the Negishi reaction, see: Smith, A. B., III; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qiu, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 8654.
    • For precedent speculation regarding the formation of mixed tert-butylalkylzinc species in the Negishi reaction, see: Smith, A. B., III; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qiu, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 8654.
  • 20
  • 21
    • 59849102131 scopus 로고    scopus 로고
    • The cross-coupling product 6 was contaminated with the inseparable deiodination compound derived from 8.
    • The cross-coupling product 6 was contaminated with the inseparable deiodination compound derived from 8.
  • 24
    • 0141712450 scopus 로고    scopus 로고
    • The use of 1,4-diazabicyclo[2.2.2]octane (DABCO) was essential to mediate dihydroxylation of the 1,1′-disubstituted olefin in 6; see: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
    • (b) The use of 1,4-diazabicyclo[2.2.2]octane (DABCO) was essential to mediate dihydroxylation of the 1,1′-disubstituted olefin in 6; see: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
  • 28
    • 59849123160 scopus 로고    scopus 로고
    • The stereo-outcome of this process was elucidated after the subsequent dithiane removal step
    • The stereo-outcome of this process was elucidated after the subsequent dithiane removal step.
  • 30
    • 59849106868 scopus 로고    scopus 로고
    • The minor diastereoisomers were easily separated during column chromatography
    • The minor diastereoisomers were easily separated during column chromatography.


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