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Volumn , Issue 5, 2008, Pages 712-714

Facile synthesis of the C1-C13 fragment of lyngbouilloside

a CNRS (France)

Author keywords

Cross metathesis; Crotyltitanation; Lyngbouilloside

Indexed keywords

CARBOXYLIC ACID; CITRAMALIC ACID; LYNGBOUILLOSIDE; MACROLIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION;

EID: 41349107839 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042805 Document Type: Article

Times cited : (18)

References (19)

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9
- 41349114188
- Compound 3: [α]D20 -26.2 (c 1.0, CHCl3, 1N MR (C6D6, δ, 7.29 (d, J, 8.8 Hz, 2 H, 6.90 (d, J, 8.8 Hz, 2 H, 5.92-5.83 (m, 1 H, 5.19-5.14(m, 2 H, 4.47 (d, J, 11.0 Hz, 1 H, 4.25 (d, J, 11.0 Hz, 1 H, 3.96 (d, J, 8.5 Hz, 1 H, 3.77 (d, J, 8.5 Hz, 1 H, 3.69 (m, 1 H, 3.41 (s, 3 H, 2.74 (m, 1 H, 1.92 (dd, J, 14.3, 3.0 Hz, 1 H, 1.85 (dd, J, 14.3, 9.3 Hz, 1 H, 1.54 (s, 3 H, 1.50 (s, 3 H, 1.40 (s, 3 H, 1.15 (d, J, 7.0 Hz, 3 H, 13C NMR (C6D6, δ, 159.7 (Cq, 141.0 (CH, 131.2 (Cq, 129.5(CH, 114.9(CH2, 114.1 (CH, 108.6 (C q, 80.8 (Cq, 79.3 (CH, 75.8 (CH2, 70.7 (CH2, 54.8 (CH3, 40.5 (CH2, 39.5 (CH, 27.6 (CH3, 27.4 (CH3, 25.0 CH3, 12.8
- 4: 357.2036; found 357.2035.

10
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12
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15
- 41349091202
- Compound 4: [α]D20 +19.0 (c 1.0, CHCl3, 1NMR (CDCl3, δ, 6.30 (dd, J, 17.8, 10.3 Hz, 1 H, 6.19 (d, J, 17.8 Hz, 1 H, 5.88 (d, J, 10.3 Hz, 1 H, 5.29 (s, 1 H, 4.34 (m, 1 H, 2.80-2.67 (m, 2 H, 2.44-2.29 (m, 2 H, 1.64 (s, 3 H, 1.63 (s, 3 H, 1.50 (br s, 1 H, 13C NMR (CDCl3, δ, 200.3 (Cq, 168.3 (Cq, 161.0 (Cq, 136.4 (CH, 129.8 (CH2, 106.7 (Cq, 95.5 (CH, 64.7 (CH, 45.1 (CH2, 40.5 (CH2, 25.5 (CH3, 24.6 CH3, ESI-HRMS: m/z calcd for C12H16NaO5: 263.0890; found 263.0885
- 5: 263.0890; found 263.0885.

16
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- Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
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- Garber, S.B.¹ Kingsbury, J.S.² Gray, B.L.³ Hoveyda, A.H.⁴

17
- 41349086822
- Compound 9: [α]D20 -11.5 (c 1.0, CHCl3, 1H NMR (C6D6, δ, 7.34 (d, J, 8.8 Hz, 2 H, 6.92 (d, J, 8.8 Hz, 2 H, 5.42 (s, 1 H, 4.52 (d, J, 11.0 Hz, 1 H, 4.34 (d, J, 11.0 Hz, 1 H, 4.27 (m, 1 H, 3.97 (d, J, 8.5 Hz, 1 H, 3.70 (d, J, 8.5 Hz, 1 H, 3.65 (m, 1 H, 3.44 (s, 3 H, 3.17 (br s, 1 H, 2.26-2.11 (m, 5 H, 2.03-1.94 (m, 3 H, 1.84 (m, 2 H, 1.66 (m, 1 H, 1.55 (s, 3 H, 1.52 (s, 3 H, 1.46 (s, 3 H, 1.45 (s, 3 H, 1.42 (s, 3 H, 0.98 (d, J, 6.7 Hz, 3 H, 13C NMR (C6D6, δ, 209.7 (C q, 168.0 (Cq, 160.1 (Cq, 159.7 (C q, 131.2 (Cq, 129.5 (CH, 114.1 (CH2, 108.6 (Cq, 106.3 (Cq, 96.1 (CH, 80.8 (Cq, 79.2 (CH, 75.9 (CH2, 70.6 (CH2, 64.9 (CH2, 54.8 CH3
- 9: 571.2878; found: 571.2870.

18
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- Bode, S. E.; Wolberg, M.; Müller, M. Synthesis 2006, 4, 557.
- (2006) Synthesis , vol.4 , pp. 557
- Bode, S.E.¹ Wolberg, M.² Müller, M.³

19
- 41349095856
- Compound 2: [α]D20 -21.8 (c 0.15, CHCl3, 1H NMR (C6D6, δ, 7.34 (d, J, 8.8, 2 H, 6.92 (d, J, 8.8 Hz, 2 H, 5.42 (s, 1 H, 4.52 (d, J, 11.0 Hz, 1 H, 4.34 (d, J, 11.0 Hz, 1 H, 4.28 (m, 1 H, 3.97 (d, J, 8.5 Hz, 1 H, 3.81 (d, J, 8.5 Hz, 1 H, 3.65 (m, 1 H, 3.44 (s, 3 H, 3.17 (br s, 1 H, 2.25-2.10 (m, 5 H, 2.03-1.90 (m, 3 H, 1.84 (m, 2 H, 1.67 (m, 1 H, 1.55 (s, 3 H, 1.52 (s, 3 H, 1.46 (s, 3 H, 1.45 (s, 3 H, 1.42 (s, 3 H, 0.98 (d, J, 6.7 Hz, 3 H, 13C NMR (C6D6, δ, 209.7 (Cq, 168.0 (C q, 160.1 (Cq, 159.7 (Cq, 131.2 (C q, 129.5 (CH, 114.1 (CH, 108.6 (Cq, 106.3 (C q, 96.1 (CH, 80.8 (Cq, 79.2 (CH, 75.9 (CH 2, 70.6 (CH2, 65.0 (CH, 54.8 (CH3, 48.4 CH2
- 9: 573.3034; found: 573.3024.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.