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Volumn 52, Issue 15, 2013, Pages 4078-4087

Strained alkenes in natural product synthesis

Author keywords

distortion; natural products; strain release; strained alkenes; total synthesis

Indexed keywords

HIGH REACTIVITY; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; STRAIN RELEASE; STRAINED MOLECULES; SYNTHETIC TRANSFORMATIONS; TOTAL SYNTHESIS;

EID: 84875836607     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207712     Document Type: Review
Times cited : (56)

References (116)
  • 10
    • 80055016474 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 10366-10368
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 10366-10368
  • 16
    • 84875831633 scopus 로고    scopus 로고
    • For reviews on the use of strained alkenes in bioconjugation applications, see
    • For reviews on the use of strained alkenes in bioconjugation applications, see
  • 18
    • 70349917806 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 6974-6998
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6974-6998
  • 23
    • 84875829766 scopus 로고
    • Strain and Its Implication in Organic Chemistry":, 273
    • "Strain and Its Implication in Organic Chemistry":, K. J. Shea, NATO ASI Ser. Ser. C 1989, 273, 133-141
    • (1989) NATO ASI Ser. Ser. C , pp. 133-141
    • Shea, K.J.1
  • 25
    • 84875872277 scopus 로고    scopus 로고
    • For recent examples illustrating progress in cyclopropene formation, see
    • For recent examples illustrating progress in cyclopropene formation, see
  • 27
    • 44949252172 scopus 로고    scopus 로고
    • for a recent example showcasing trans-cyclooctene synthesis, see
    • N. Yan, X. Liu, M. K. Pallerla, J. M. Fox, J. Org. Chem. 2008, 73, 4283-4286; for a recent example showcasing trans-cyclooctene synthesis, see
    • (2008) J. Org. Chem. , vol.73 , pp. 4283-4286
    • Yan, N.1    Liu, X.2    Pallerla, M.K.3    Fox, J.M.4
  • 28
    • 41149117469 scopus 로고    scopus 로고
    • for recent examples of forming highly strained bridgehead alkenes, see
    • M. Royzen, G. P. A. Yap, J. M. Fox, J. Am. Chem. Soc. 2008, 130, 3760-3761; for recent examples of forming highly strained bridgehead alkenes, see
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 3760-3761
    • Royzen, M.1    Yap, G.P.A.2    Fox, J.M.3
  • 31
    • 80052848426 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 9177-9179.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9177-9179
  • 51
    • 84985599336 scopus 로고
    • For the use of simple methylenecyclopropane derivatives in intermolecular [4+2] cycloadditions, see:, and references within; for a pressure-promoted methylenecyclopropane intramolecular Diels-Alder cycloaddition, see
    • For the use of simple methylenecyclopropane derivatives in intermolecular [4+2] cycloadditions, see:, F. E. Meyer, K. H. Ang, A. G. Steinig, A. DeMeijere, Synlett 1994, 191 and references within; for a pressure-promoted methylenecyclopropane intramolecular Diels-Alder cycloaddition, see
    • (1994) Synlett , pp. 191
    • Meyer, F.E.1    Ang, K.H.2    Steinig, A.G.3    Demeijere, A.4
  • 54
    • 84865473905 scopus 로고    scopus 로고
    • For a current article discussing the origin of the remarkable reactivity of cyclobutadiene, see:, and references therein.
    • For a current article discussing the origin of the remarkable reactivity of cyclobutadiene, see:, J. I. Wu, Y. Mo, F. A. Evangelista, P. v. R. Schleyer, Chem. Commun. 2012, 48, 8437-8439, and references therein.
    • (2012) Chem. Commun. , vol.48 , pp. 8437-8439
    • Wu, J.I.1    Mo, Y.2    Evangelista, F.A.3    Schleyer V. P, R.4
  • 56
    • 0029825282 scopus 로고    scopus 로고
    • for mechanistic insights into the intramolecular cycloaddition of cyclobutadiene, see
    • J. A. Tallarico, M. L. Randall, M. L. Snapper, J. Am. Chem. Soc. 1996, 118, 9196-9197; for mechanistic insights into the intramolecular cycloaddition of cyclobutadiene, see
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9196-9197
    • Tallarico, J.A.1    Randall, M.L.2    Snapper, M.L.3
  • 64
    • 44949142369 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3054-3056
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3054-3056
  • 66
    • 84875866656 scopus 로고    scopus 로고
    • For current reviews discussing the vinigrol challenge and previous synthetic approaches, see
    • For current reviews discussing the vinigrol challenge and previous synthetic approaches, see
  • 71
    • 84875870289 scopus 로고    scopus 로고
    • DOI:, and references cited therein.
    • For a current article discussing the reasoning behind the exceptional reactivity of norbornenes, see: S.A. Lopez, K.N. Houk, J. Org. Chem. 2013, DOI:, and references cited therein.
    • (2013) J. Org. Chem
    • Lopez, S.A.1    Houk, K.N.2
  • 83
    • 84875840233 scopus 로고    scopus 로고
    • For reviews on cyclopropene and methylenecyclopropane derivatives in transition-metal-catalyzed reactions, see
    • For reviews on cyclopropene and methylenecyclopropane derivatives in transition-metal-catalyzed reactions, see
  • 88
    • 35048841685 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7364-7376
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7364-7376
  • 89
    • 80055024590 scopus 로고    scopus 로고
    • for recent work utilizing the strained alkene norbornene as a shuttle for C-H bond functionalization, see
    • Z. Zhu, Y. Wei, M. Shi, Chem. Soc. Rev. 2011, 40, 5534-5563; for recent work utilizing the strained alkene norbornene as a shuttle for C-H bond functionalization, see
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 5534-5563
    • Zhu, Z.1    Wei, Y.2    Shi, M.3
  • 94
    • 36749093348 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8854-8857.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8854-8857
  • 105
    • 38349151655 scopus 로고    scopus 로고
    • for an early example of a Pauson-Khand reaction in total synthesis employing a strained cyclobutene, see
    • M. K. Pallerla, J. M. Fox, Org. Lett. 2007, 9, 5625-5628; for an early example of a Pauson-Khand reaction in total synthesis employing a strained cyclobutene, see
    • (2007) Org. Lett. , vol.9 , pp. 5625-5628
    • Pallerla, M.K.1    Fox, J.M.2
  • 107
    • 84875820358 scopus 로고    scopus 로고
    • Highly substituted alkenes are unable to compete with other alkyne molecules for cobaltacycle formation because of steric hindrance around the double bond. For references, see
    • Highly substituted alkenes are unable to compete with other alkyne molecules for cobaltacycle formation because of steric hindrance around the double bond. For references, see
  • 112
  • 116
    • 84982382854 scopus 로고
    • for more recent discussions on the reactivity of trans-cyclooctenes, see references[11] and [8a].
    • Angew. Chem. Int. Ed. Engl. 1974, 13, 604-606; for more recent discussions on the reactivity of trans-cyclooctenes, see references[11] and [8a].
    • (1974) Angew. Chem. Int. Ed. Engl. , vol.13 , pp. 604-606


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