메뉴 건너뛰기




Volumn 10, Issue 6, 2004, Pages 1527-1544

Strategy for Enantio- and Diastereoselective Syntheses of All Possible Stereoisomers of 1,3-Polyol Arrays Based on a Highly Catalyst-Controlled Epoxidation of α,β-Unsaturated Morpholinyl Amides: Application to Natural Product Synthesis

Author keywords

Asymmetric synthesis; Diastereoselectivity; Epoxidation; Morpholinyl amide; Polyols

Indexed keywords

AMINES; CATALYSTS; COMPLEXATION; ISOMERS; STEREOCHEMISTRY;

EID: 1842614850     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305709     Document Type: Article
Times cited : (51)

References (145)
  • 5
    • 0001484625 scopus 로고    scopus 로고
    • a) C. Schenider, Angew. Chem. 1998, 110, 1445; Angew. Chem. Int. Ed. 1998, 37, 1375;
    • (1998) Angew. Chem. , vol.110 , pp. 1445
    • Schenider, C.1
  • 6
    • 0032486344 scopus 로고    scopus 로고
    • a) C. Schenider, Angew. Chem. 1998, 110, 1445; Angew. Chem. Int. Ed. 1998, 37, 1375;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1375
  • 7
    • 0141548942 scopus 로고    scopus 로고
    • b) W. H. Hoffmann, Angew. Chem. 2003, 115, 1128; Angew. Chem. Int. Ed. 2003, 42, 1096.
    • (2003) Angew. Chem. , vol.115 , pp. 1128
    • Hoffmann, W.H.1
  • 8
    • 0037429883 scopus 로고    scopus 로고
    • b) W. H. Hoffmann, Angew. Chem. 2003, 115, 1128; Angew. Chem. Int. Ed. 2003, 42, 1096.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1096
  • 13
    • 0034658716 scopus 로고    scopus 로고
    • d) V. Narkevitch, K. Schenk, P. Vogel, Angew. Chem. 2000, 112, 1876; Angew. Chem. Int. Ed. 2000, 39, 1806;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1806
  • 16
    • 0003445429 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York
    • b) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999;
    • (1999) Comprehensive Asymmetric Catalysis
  • 17
    • 0003544583 scopus 로고    scopus 로고
    • (Ed: I. Ojima), 2nd ed., Wiley, New York
    • c) Catalytic Asymmetric Synthesis (Ed: I. Ojima), 2nd ed., Wiley, New York, 2000.
    • (2000) Catalytic Asymmetric Synthesis
  • 43
    • 0035800404 scopus 로고    scopus 로고
    • c) S. J. O'Malley, J. L. Leighton, Angew. Chem. 2001, 113, 2999; Angew. Chem. Int. Ed. 2001, 40, 2915;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2915
  • 54
    • 0034658716 scopus 로고    scopus 로고
    • g) V. Narkevitch, K. Shenk, P. Vogel, Angew. Chem. 2000, 112, 1876; Angew. Chem. Int. Ed. 2000, 39, 1806;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1806
  • 57
    • 0030733069 scopus 로고    scopus 로고
    • For recent examples of allyl addition using chiral borane or titanium reagents in 1,3-polyol syntheses, see: a) I. Paterson, D. J. Wallace, K. R. Gibson, Tetrahedron Lett. 1997, 38, 8911;
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8911
    • Paterson, I.1    Wallace, D.J.2    Gibson, K.R.3
  • 67
    • 1842613845 scopus 로고    scopus 로고
    • note
    • Due to the difficulty in classifying total syntheses into the above-mentioned categories, they are classified only according to the target natural products.
  • 78
    • 0035801646 scopus 로고    scopus 로고
    • C. J. Sinz, S. D. Rychnovsky, Angew. Chem. 2001, 113, 3324; Angew. Chem. Int. Ed. 2001, 40, 3224.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3224
  • 87
    • 0034599684 scopus 로고    scopus 로고
    • c) I. Paterson, V. A. Doughty, M. D. McLeod, T. Trieselmann, Angew. Chem. 2000, 112, 1364; Angew. Chem. Int. Ed. 2000, 39, 1308;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1308
  • 92
    • 84985530075 scopus 로고
    • b) S. Masamune, W. Choy, J. S. Peterson, L. S. Sita, Angew. Chem. 1985, 97, 1; Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1
  • 97
    • 0142087735 scopus 로고    scopus 로고
    • for the use of α,β-unsaturated N-acylpyrrole as a substrate, see: d) T. Kinoshita, T. Okada, S.-R. Park, S. Matsunaga, M. Shibasaki, Angew. Chem. 2003, 115, 4828; Angew. Chem. Int. Ed. 2003, 42, 4680-4684.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4680-4684
  • 107
    • 1842457224 scopus 로고    scopus 로고
    • note
    • Our catalyst system was applicable to substrates that were functionalized with a C-C double bond or a ketone, without overoxidation. See: refs. [31] and [32].
  • 108
    • 1842457227 scopus 로고    scopus 로고
    • note
    • The α,β-epoxy peroxy ester 3 is a stable compound that was isolated using common flash column chromatography and can be stored for at least two months at 4°C.
  • 117
    • 0037122049 scopus 로고    scopus 로고
    • c) S. N. Goodman, E. N. Jacobsen, Angew. Chem. 2002, 114, 4897; Angew. Chem. Int. Ed. 2002, 41, 4703.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4703
  • 118
    • 1842613844 scopus 로고    scopus 로고
    • note
    • For details, see Supporting Information.
  • 121
    • 1842509444 scopus 로고    scopus 로고
    • note
    • 2TiCl that functions via single electron transfer proceeded sluggishly.
  • 122
    • 1842509446 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.
  • 124
    • 1842613843 scopus 로고    scopus 로고
    • note
    • Although diol anti-24a was isolated by preparative thin-layer chromatography, a mixture of diastereomers was used to supply a large amount of substrate for further transformation.
  • 125
    • 1842457222 scopus 로고    scopus 로고
    • note
    • Enantioselectivity or diastereoselectivity was determined by HPLC analysis.
  • 128
    • 1842457219 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis, the ratio of diastereomers was determined to be >95:5.
  • 129
    • 1842613842 scopus 로고    scopus 로고
    • note
    • McDonald et al. reported a very versatile strategy for syntheses of the 1,3-polyol array without stereochemical limitation and demonstrated stereoselective syntheses of 1,3,5,7-tetraols and 1,3,5,7,9-pentaols. Five of eight possible stereoisomers with several of their enantiomers were synthesized. See Supporting Information for ref. [20]c.
  • 131
    • 1842561823 scopus 로고    scopus 로고
    • note
    • The absolute configuration was determined using Mosher's method. For details, see Supporting Information.
  • 132
    • 1842561822 scopus 로고    scopus 로고
    • note
    • When acetonide was used as the protecting group, unsatisfactory results were obtained in the following stereoselective ketone reduction (up to β-OH: α-OH 3:1) even after various attempts.
  • 134
    • 0032580376 scopus 로고    scopus 로고
    • For representative reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413;
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 135
    • 0000785058 scopus 로고    scopus 로고
    • b) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem. , vol.112 , pp. 3140
    • Fürstner, A.1
  • 136
    • 0001399412 scopus 로고    scopus 로고
    • b) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012
  • 140
    • 1842457216 scopus 로고    scopus 로고
    • note
    • Enantiomeric excess was determined by HPLC analysis after conversion to the corresponding ketone with benzylmagnesium chloride.
  • 141
    • 1842457218 scopus 로고    scopus 로고
    • note
    • Due to the volatility profile of the corresponding ethyl ester of 61, butyl ester was used instead of ethyl ester. When the lithium enolate of the Weinreb amide was used, a slow reaction and moderate conversion were obtained.
  • 142
    • 1842613836 scopus 로고    scopus 로고
    • note
    • Because of the ease of detection by HPLC analysis, benzylidene acetal was used as a protecting group of diol.
  • 144
    • 1842561818 scopus 로고    scopus 로고
    • note
    • There might be an experimental error or an impurity problem.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.