Studies towards a total synthesis of Sarains A-C. Stereospecific condensation of α,β-unsaturated esters with the phenyl oxazoline derivative of threonine

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1273-1276

  Jaroch, Stefan ^a   Matsuoka, Richard T ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ESTER; GLUTAMIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE; SARAIN A; SARAIN B; SARAIN C; THREONINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033547984     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02639-2     Document Type: Article

References (29)

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2. Current address: Department of Synthetic Chemistry, SmithKline Beecham, 709 Swedeland Rd., Box 1539, King Of Prussia, PA 19406.
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7. For brief reviews, see: (a) Kobayashi, J.; Ishibashi, M. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1992; Vol. 41, Chapter 2.
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15. The study described in reference 7 was carried out in the ent series. For clarity it is depicted in the natural series in Scheme 1.
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18. Since C-5 of oxazoline 7 possesses the S configuration, these model studies were also in the series enantiomeric to the natural sarain alkaloids.
19. The enoates were synthesized from 1,3-propanediol by monosilylation (McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388), Swern oxidation (Swern, D.; Mancuso, A. J. Synthesis 1981, 165) and Homer-Wittig reaction either with triethyl phosphonoacetate or methyl [bis(2,2,2-trifluoroethyl)phosphono]acetate (Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405).
20. The enoates were synthesized from 1,3-propanediol by monosilylation (McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388), Swern oxidation (Swern, D.; Mancuso, A. J. Synthesis 1981, 165) and Homer-Wittig reaction either with triethyl phosphonoacetate or methyl [bis(2,2,2-trifluoroethyl)phosphono]acetate (Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405).
21. The enoates were synthesized from 1,3-propanediol by monosilylation (McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388), Swern oxidation (Swern, D.; Mancuso, A. J. Synthesis 1981, 165) and Homer-Wittig reaction either with triethyl phosphonoacetate or methyl [bis(2,2,2-trifluoroethyl)phosphono]acetate (Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405).
22. Oxazoline 7 was prepared by treatment of methyl N-benzoyl-(L)-threoninate with thionyl chloride: Elliot, D.F. J. Chem. Soc. 1950, 62.
23. 1H NMR analysis.
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25. 7.
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28. Enoate 14 was obtained by addition of phthalimide to acrolein (Taber, D. F.; Hoerrner, R. S.; Hagen, M. D. J. Org. Chem. 1991, 56, 1287) followed by reaction with methyl [bis(2,2,2-trifluoroethyl)phosphono]acetate (Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405).
29. Wolfe S.; Kasan, S. K. Can. J. Chem. 1970, 48, 3572.