S(N)Ar macrocyclisation: A new approach towards the synthesis of D-O-E- segment of vancomycin

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7433-7436

  Rama Rao, A V ^a   Gurjar, M K ^a   Lakshmipathi, P ^a   Reddy, M M ^a   Nagarajan, M ^a   Pal, Shashwati ^a   Sarma, B V N B S ^a   Tripathy, N K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

VANCOMYCIN;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030801370     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01749-8     Document Type: Article

References (13)

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2. Zhu, J. Syn. Lett., 1997, 133-144.
3. Bois-choussy, M.; Beugelmans, R.; Bouillon, J.P.; Zhu, J. Tetrahedron Lett., 1995, 36, 4781-4784.
4. Beugelmans, R.; Bois-choussy, M.; Vergne, C.; Bouillon, J.P.; Zhu, J. J. Chem. Soc., Chem. Commun., 1996, 1029-1030.
5. Boger, D.L.; Borzilleri, R.M.; Nukui, S. Bioorganic Med. Chem. Lett., 1995, 5, 3091-3096.
6. Evans, D.A.; Watson, P.S. Tetrahedron Lett., 1996, 37, 3251-3254.
7. Evans, D.A.; Barrow, J.C.; Watson, P.S.; Ratz, A.M.; Dinsmore, C.J.; Evrard, D.A.; DeVries, K.M.; Ellman, J.A.; Rychnovsky, S.D.; Lacour, J. J. Am. Chem. Soc., 1997, 119, 3419-3420.
8. Rama Rao, A.V.; Reddy, K.L.; Rao, A.S. Tetrahedron Lett., 1994, 35, 8465-8469.
9. Williams, L.; Zhang, Z.; Shao, F.; Carroll, P.J.; Joullie, M.M. Tetrahedron, 1996, 52, 11673-11694.
10. 2O) sequence.
11. Butcher, M.; Mathews, R.J.; Middleton, S. Aust. J. Chem., 1973, 26, 2067-2069.
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13. M++1). Compound 16 : δ 8.04 (dd, l H, J = 7.2,8.5 Hz), 7.58 (bs, 1H), 7.2 - 7.4 (m, 4 H), 7.06 (d, 1 H, J = 8.5 Hz), 6.61 (bd, 1 H, J = 8.5 Hz), 5.87 (bs, 1 H), 5.18 (m, 1 H), 5.03 (d, 2 H, J = 5.3 Hz), 4.72 (m, 1 H), 4.18 (t, 1 H, J = 4.9 Hz), 3.75 (m, 2 H), 3.48 (s, 3 H), 3.06 (dd, 1 H, J = 4.9, 16.5 Hz), 2.66 (dd, 1 H, J = 6.6, 16.5 Hz), 1.38 (s, 9 H), 0.91 (s, 9 H), 0.1 (s, 3 H), -0.1 (s, 3 H). FABMS : m/z 737 (M+). Compound 17 : more polar isomer : δ 8.01 (d, 1 H, J = 8.4 Hz), 7.5 (dd, 1H, J = 2.0, 8.4 Hz), 7.41 (d, 1 H, J = 8.4 Hz), 7.35 (d, l H, J = 2.0 Hz), 7.01 (d, 1 H, J = 8.4 Hz), 6.87 (d, 1 H, J = 7.1 Hz), 6.72 (bs, 1 H), 6.12 (s, 1 H), 5.35-5.5 (m, 2 H), 4.9 (m, 1 H), 4.57-4.72 (m, 2 H), 3.77 (m, 2 H), 3.32 (s, 3 H), 3.05 (dd, 1 H, J = 4.2, 16.4 Hz), 2.87 (bs, 1 H), 2.67 (dd, 1 H, J = 6.9, 16.4 Hz), 1.49 (s, 9 H). FABMS : m/z 603 (M+) : less polar isomer : δ 8.04 (d, 1 H, J = 8.4 Hz), 7.75 (d, 1H, J = 2.0 Hz), 7.12-7.3 (m, 2 H), 7.02 (dd, 1 H, J = 2.0, 8.4 Hz), 6.75 (m, 1 H), 6.01 (d, 1 H, J = 2.0 Hz), 5.62 (d, 1 H, J = 7.1 Hz), 5.5 (m, 1 H), 5.08 (m, 1 H), 4.72 (m, 1 H), 4.62 (m, 1 H), 3.72 (d, 2 H, J = 4.2 Hz), 3.32 (s, 3 H), 3.20 (dd, 1 H, J = 4.5, 16.4 Hz), 2.79 (m, 1 H), 2.59 (dd, 1 H, J = 6.4, 16.4 Hz), 1.50 (s, 9 H). FABMS : m/z 603 (M+).