Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3671-3674

  Hamper, Bruce C ^a   Dukesherer, Daniel R ^a   South, Michael S ^a  

^a MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0029944026     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00659-4     Document Type: Article

References (18)

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9. For references to solution phase azomethine ylide cyclizations using alpha-amino esters see: (a) Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 231-349.
10. (b) Grigg, R. Chem. Soc. Rev. 1987, 16, 89-121.
11. (c) Barr, D. A.; Grigg, R.; Gunaratne, H. Q. N.; Kemp, J.; McMeekin, P.; Sridharan, V. Tetrahedron 1988, 44, 557-70.
12. (d) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384-91.
13. The solid-phase library synthesis of proline analogs 1 will be reported elsewhere.
14. Hughes, D. L. 1992. The Mitsunobu Reaction. Organic Reactions 42, 335-656.
15. Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193-6.
16. A TFA cleavable ether link has been prepared indirectly by solution phase Mitsunobu coupling followed by attachment of an activated ester to an aminomethylated polystyrene resin. Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-7.
17. 2, and ether. The resin was collected and washed with diethyl ether and dried in vacuo to afford 15.25 g of 2a. A loading of 0.70 meq/g was determined by quantitative measurement of the cleaved material.
18. 1H NMR (DMSO) δ 1.61 (s, 3H), 2.83 (s, 3H), 3.48 (d, 1H), 3.75 (t, 1H), 4.28 (b, 2H), 4.89 (d, 1H), 6.82 (d, 1H), 6.90 (t, 1H), 7.24 (m, 1H), 7.30 (d, 1H). HRMS (FAB+): Calculated, 379.1505; Observed, 379.1522.