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Volumn 54, Issue 1, 2015, Pages 215-220

Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: A concise route to (+)-neopeltolide

Author keywords

Catalysis; Enantioselective synthesis; Leucascandrolide a; Neopeltolide; Olefin metathesis

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; MOLECULES; MOLYBDENUM COMPOUNDS; OLEFINS; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY; TUNGSTEN COMPOUNDS;

EID: 84920135535     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409120     Document Type: Article
Times cited : (66)

References (86)
  • 1
    • 22744448499 scopus 로고    scopus 로고
    • For reviews regarding the use of catalytic OM reactions in natural product synthesis, see
    • For reviews regarding the use of catalytic OM reactions in natural product synthesis, see: a) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4490-4527
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4490-4527
  • 4
    • 84902089766 scopus 로고    scopus 로고
    • for overviews regarding macrocyclic RCM reactions and their utility in natural product synthesis
    • c) A. H. Hoveyda, J. Org. Chem. 2014, 79, 4763-4792; for overviews regarding macrocyclic RCM reactions and their utility in natural product synthesis
    • (2014) J. Org. Chem. , vol.79 , pp. 4763-4792
    • Hoveyda, A.H.1
  • 5
    • 84878855576 scopus 로고    scopus 로고
    • see: (Eds: J. Cossy, S. C. Meyer), Wiley-VCH, Weinheim
    • see: d) A. Gradillas, J. Pérez-Castells, Metathesis in Natural Product Synthesis (Eds: J. Cossy, S. C. Meyer), Wiley-VCH, Weinheim, 2010, pp. 149 - 182.
    • (2010) Metathesis in Natural Product Synthesis , pp. 149-182
  • 6
    • 67749135570 scopus 로고    scopus 로고
    • For Z-selective ROCM reactions promoted by Mo alkylidenes, see
    • For Z-selective ROCM reactions promoted by Mo alkylidenes, see: a) I. Ibrahem, M. Yu, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 3844-3845
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3844-3845
  • 8
    • 84864450911 scopus 로고    scopus 로고
    • for Z-selective ROCM reactions catalyzed by Ru carbene complexes see
    • for Z-selective ROCM reactions catalyzed by Ru carbene complexes see: c) R. M. K. Khan, R. V. O'Brien, S. Torker, B. Li, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 12774-12779
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 12774-12779
  • 12
    • 84903845542 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 1999-2003
    • (2014) Angew. Chem. , vol.126 , pp. 1999-2003
  • 14
    • 84920147424 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 3966-3969.
    • (2014) Angew. Chem. , vol.126 , pp. 3966-3969
  • 15
    • 79953031273 scopus 로고    scopus 로고
    • For Z-selective CM reactions with Mo or W alkylidene complexes, see
    • For Z-selective CM reactions with Mo or W alkylidene complexes, see: a) S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461-466
    • (2011) Nature , vol.471 , pp. 461-466
  • 18
    • 84889820398 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 8553-8558
    • (2013) Angew. Chem. , vol.125 , pp. 8553-8558
  • 19
    • 84871978691 scopus 로고    scopus 로고
    • for Z-selective CM reactions with Ru complexes, see
    • for Z-selective CM reactions with Ru complexes, see: d) M. B. Herbert, V. M. Marc, R. L. Pederson, R. H. Grubbs, Angew. Chem. Int. Ed. 2013, 52, 310-314
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 310-314
  • 22
    • 80455177350 scopus 로고    scopus 로고
    • For Z-selective MRCM reactions with Mo or Wcomplexes, see
    • For Z-selective MRCM reactions with Mo or Wcomplexes, see: a) M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature 2011, 479, 88-93
    • (2011) Nature , vol.479 , pp. 88-93
  • 26
    • 84873815391 scopus 로고    scopus 로고
    • for Z-selective RCM reactions with Ru carbene complexes, see
    • for Z-selective RCM reactions with Ru carbene complexes, see: d) L. E. Rosebrugh, M. B. Herbert, V. M. Marx, B. K. Keitz, R. H. Grubbs, J. Am. Chem. Soc. 2013, 135, 1276-1279.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 1276-1279
  • 27
    • 37349010312 scopus 로고    scopus 로고
    • For previous enantioselective approaches to the total synthesis of neopeltolide, see
    • For previous enantioselective approaches to the total synthesis of neopeltolide, see: a)W. Youngsaye, J. T. Lowe, F. Pohlke, P. Ralifo, J. S. Panek, Angew. Chem. Int. Ed. 2007, 46, 9211-9214
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 9211-9214
  • 38
    • 84920152215 scopus 로고    scopus 로고
    • for the corresponding formal syntheses, see the Supporting Information
    • for the corresponding formal syntheses, see the Supporting Information.
  • 39
    • 0034722988 scopus 로고    scopus 로고
    • For previous enantioselective approaches to the total synthesis of leucascandrolide A, see
    • For previous enantioselective approaches to the total synthesis of leucascandrolide A, see: a) K. R. Hornberger, C. L. Hamblett, J. L. Leighton, J. Am. Chem. Soc. 2000, 122, 12894-12895
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12894-12895
  • 45
    • 0035804955 scopus 로고    scopus 로고
    • For approaches to the stereoselective synthesis of the neopeltolide/ leucascandrolide A side chain (other than those in Ref. [5, 6]), see
    • For approaches to the stereoselective synthesis of the neopeltolide/ leucascandrolide A side chain (other than those in Ref. [5, 6]), see: P. Wipf, T. H. Graham, J. Org. Chem. 2001, 66, 3242-3245.
    • (2001) J. Org. Chem. , vol.66 , pp. 3242-3245
  • 46
    • 36049015757 scopus 로고    scopus 로고
    • For challenges in catalytic OM reactions, see
    • For challenges in catalytic OM reactions, see: a) A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251
    • (2007) Nature , vol.450 , pp. 243-251
  • 47
    • 84889847822 scopus 로고    scopus 로고
    • b) A. Fürstner, Science 2013, 341, 1357-1364.
    • (2013) Science , vol.341 , pp. 1357-1364
    • Fürstner, A.1
  • 48
    • 73349084323 scopus 로고    scopus 로고
    • For a discussion of the use of chiral catalysts for addressing problems other than enantioselectivity, see
    • For a discussion of the use of chiral catalysts for addressing problems other than enantioselectivity, see: A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem. Int. Ed. 2010, 49, 34-44
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 34-44
  • 49
    • 84920160836 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 38-49.
    • (2010) Angew. Chem. , vol.122 , pp. 38-49
  • 50
    • 0028924634 scopus 로고
    • For an early application of catalytic MRCM reactions to obtain a trisubstituted alkene followed by diastereoselective hydrogenation in a total synthesis, see
    • For an early application of catalytic MRCM reactions to obtain a trisubstituted alkene followed by diastereoselective hydrogenation in a total synthesis, see: A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2943-2944
  • 52
    • 84862079156 scopus 로고    scopus 로고
    • There has been a single report of boronate addition to a phenyl-substituted unsaturated Weinreb amide catalyzed by an NHC-Cu complex, where the desired product was obtained in quantitative yield and 89:11 e.r
    • a) H. Wu, S. Radomkit, J. M. O'Brien, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 8277 - 8285. There has been a single report of boronate addition to a phenyl-substituted unsaturated Weinreb amide catalyzed by an NHC-Cu complex, where the desired product was obtained in quantitative yield and 89:11 e.r.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 8277-8285
    • Wu, H.1    Radomkit, S.2    O'Brien, J.M.3    Hoveyda, A.H.4
  • 53
    • 77957665401 scopus 로고    scopus 로고
    • see
    • see: b) D. Hirsch-Weil, K. A. Abboud, S. Hong, Chem. Commun. 2010, 46, 7525-7527.
    • (2010) Chem. Commun. , vol.46 , pp. 7525-7527
  • 54
    • 84896476338 scopus 로고    scopus 로고
    • We are aware of one other example of Lewis base catalyzed boronate conjugate addition in natural product synthesis; see
    • We are aware of one other example of Lewis base catalyzed boronate conjugate addition in natural product synthesis; see: S. Radomkit, A. H. Hoveyda, Angew. Chem. Int. Ed. 2014, 53, 3387-3391
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 3387-3391
  • 57
    • 84864282511 scopus 로고    scopus 로고
    • for a recent review, see
    • for a recent review, see: b) K. J. Ralston, A. N. Hulme, Synthesis 2012, 44, 2310-2324.
    • (2012) Synthesis , vol.44 , pp. 2310-2324
  • 58
    • 0026579593 scopus 로고
    • For representative auxiliary-based diastereoselective acetate aldol additions, see
    • For representative auxiliary-based diastereoselective acetate aldol additions, see: a)W. Oppolzer, C. Starkemann, Tetrahedron Lett. 1992, 33, 2439-2442
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2439-2442
  • 61
    • 0034704636 scopus 로고    scopus 로고
    • for conversion into a Weinreb amide, see
    • for conversion into a Weinreb amide, see: d) M. T. Crimmins, K. Chaudhary, Org. Lett. 2000, 2, 775-777.
    • (2000) Org. Lett. , vol.2 , pp. 775-777
  • 62
    • 84920192696 scopus 로고    scopus 로고
    • The requisite oxabicycle was prepared in four steps from commercially available materials; see the Supporting Information for details
    • The requisite oxabicycle was prepared in four steps from commercially available materials; see the Supporting Information for details.
  • 63
    • 84920141576 scopus 로고    scopus 로고
    • The minor diastereoisomer from enantioselective boronate conjugate addition (95:5 e.r.) was removed by column chromatography on silica gel of ester 9
    • The minor diastereoisomer from enantioselective boronate conjugate addition (95:5 e.r.) was removed by column chromatography on silica gel of ester 9.
  • 67
    • 84920142534 scopus 로고    scopus 로고
    • see Ref. 9
    • see Ref. 9.
  • 70
    • 33746494445 scopus 로고    scopus 로고
    • For reviews on Suzuki-type catalytic cross-coupling reactions, see
    • For reviews on Suzuki-type catalytic cross-coupling reactions, see: a) M. Schnürch, R. Flasik, A. F. Khan, M. Spina, M. D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem. 2006, 3283-3307
    • (2006) Eur. J. Org. Chem. , pp. 3283-3307
  • 78
    • 84920200487 scopus 로고    scopus 로고
    • For total synthesis initiatives where catalytic transformations are the principal strategic elements, see: a Ref. 10
    • For total synthesis initiatives where catalytic transformations are the principal strategic elements, see: a) Ref. 10
  • 86
    • 0001852710 scopus 로고    scopus 로고
    • for a discussion of the concept of multi-catalytic synthesis routes, see: (Eds.: F. Vogtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim
    • for a discussion of the concept of multi-catalytic synthesis routes, see: g) A. H. Hoveyda in Stimulating Concepts in Chemistry (Eds.: F. Vogtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, pp. 145 - 162.
    • (2000) Stimulating Concepts in Chemistry , pp. 145-162


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