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Synlett

Volumn , Issue 9, 2007, Pages 1375-1378

Synthesis of hydrophobically modified analogues of adenophorine

(3) Afarinkia, Kamyar a,c Bahar, Akmal a,c Neuss, Judi b

a UNIVERSITY OF BRADFORD (United Kingdom)

b UCB PHARMA (Belgium)

c KING'S COLLEGE LONDON (United Kingdom)

Author keywords

Azasugars; Diels Alder cycloaddition; Regioselectivity; Stereoselectivity; Stille reaction

Indexed keywords

3 METHYL 4 DEOXYADENOPHORINE; ADENOPHORINE DERIVATIVE; HERBACEOUS AGENT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ADENOPHORA; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; HYDROPHOBICITY; MEDICINAL PLANT; METHODOLOGY; STEREOCHEMISTRY; STILLE REACTION; SYNTHESIS;

EID: 34250743191 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-980359 Document Type: Article

Times cited : (5)

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34
- 34250768484
- Compound 17: IR (film, νmax, 1772 (s, lactone) cm-1. MS (CI, NH3, m/z, 306 (100, MH, HRMS (ESI, m/z calcd for C17H 24NO4 [MH, 306.1700; found: 306.1702. 1H NMR (360 MHz, CDCl3, δ, 1.09 (t, 3 H, J, 7.5 Hz, CH2CH3, 1.27 (s, 3 H, CH3, 1.42-1.57 (m, 1 H, CHHCH3, 1.59-1.70 (m, 1 H, CHHCH3, 1.90 (dd, 1 H, J, 2.5, 15.2 Hz, H-7 a, 2.24 (ddd, 1 H, J, 2.2, 9.7, 15.2 Hz, H-7b, 3.03 (dt, 1 H, J, 2.2, 10.4 Hz, H-6, 3.56 (s, 3 H, OCH3, 3.80 (dd, 1 H, J, 2.5, 9.7 Hz, H-8, 4.62 (d, 1 H, J, 12.3 Hz, CHHPh, 4.84 (d, 1 H, J, 12.3 Hz, CHHPh, 7.25-7.37 (m, 5 H, Ph, 13C NMR (90 MHz, CDCl3, δ, 11.2 CH 2CH3
- ipso), 169.9 (C-3).

35
- 34250742853
- Compound 5: IR (CH2Cl2, νmax, 3354 (br, OH) cm-1. MS (CI, NH3, m/z, 190 (100, MH, HRMS (ESI, calcd for C9H 20NO3 [MH, 190.1438; found: 190.1439. 1H NMR (400 MHz, CD3OD, δ, 1.17 (t, 3 H, J, 7.6 Hz, CH2CH3, 1.27 (s, 3 H, CH3, 1.56-1.66 (m, 1 H, CHHCH3, 1.68-1.82 (m, 1 H, H-4 a, 2.00-2.09 (m, 1 H, CHHCH3, 2.19 (d, 1 H, J, 4.4, 12.4 Hz, H-4b, 2.91-2.98 (m, 2 H, H-2, H-6, 3.80 (ddd, 1 H, J, 4.4, 10.5, 11.8 Hz, H-5, 3.96-3.99 (m, 2 H, CH2OH, 13C NMR (100 MHz, CD3OD, δ, 12.3 (CH2CH3, 21.8 (CH3, 22.3 (CH2CH3, 49.4 (C-4, 58.9 (CH2OH, 64.8 (C-6, 65.9 (C-2, 67.1 C-5
- 2OH), 62.9 (C-6), 64.5 (C-2), 67.4 (C-5), 70.1 (C-3).

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