메뉴 건너뛰기




Volumn 122, Issue 18, 2000, Pages 4295-4303

Total syntheses of (±) and (-)-stemoamide

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BUTENOLIDE; GAMMA CHLOROBUTRYL CHLORIDE; NICKEL CHLORIDE; OXAZOLE DERIVATIVE; PYROGLUTAMIC ACID; SODIUM BOROHYDRIDE; STEMOAMIDE; SUCCINIMIDE; UNCLASSIFIED DRUG;

EID: 0034630841     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994214w     Document Type: Article
Times cited : (110)

References (69)
  • 2
    • 0000765025 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York
    • For leading references, see: (a) Goetz, M.; Edwards, O. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1976; Vol. IX, pp 545-551. (b) Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Noxoe, S. In Natural Products Chemistry; Academic Press: New York, 1975; Vol. 2, pp 292-93. See also ref 1.
    • (1976) The Alkaloids , vol.9 , pp. 545-551
    • Goetz, M.1    Edwards, O.E.2
  • 3
    • 0000256812 scopus 로고
    • Academic Press: New York
    • For leading references, see: (a) Goetz, M.; Edwards, O. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1976; Vol. IX, pp 545-551. (b) Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Noxoe, S. In Natural Products Chemistry; Academic Press: New York, 1975; Vol. 2, pp 292-93. See also ref 1.
    • (1975) Natural Products Chemistry , vol.2 , pp. 292-293
    • Nakanishi, K.1    Goto, T.2    Ito, S.3    Natori, S.4    Noxoe, S.5
  • 4
    • 0028008367 scopus 로고
    • Ye, Y.; Qin, G.; Xu, R.-S. Phytochemistry 1994, 37, 1201, 1205. (b) Cheng, D.; Guo, J.; Chu, T. T.; Rôder, E. J. Nat. Prod. 1988, 51, 202. (c) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. See also ref 1.
    • (1994) Phytochemistry , vol.37 , pp. 1201
    • Ye, Y.1    Qin, G.2    Xu, R.-S.3
  • 5
    • 33845278132 scopus 로고
    • Ye, Y.; Qin, G.; Xu, R.-S. Phytochemistry 1994, 37, 1201, 1205. (b) Cheng, D.; Guo, J.; Chu, T. T.; Rôder, E. J. Nat. Prod. 1988, 51, 202. (c) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. See also ref 1.
    • (1988) J. Nat. Prod. , vol.51 , pp. 202
    • Cheng, D.1    Guo, J.2    Chu, T.T.3    Rôder, E.4
  • 7
    • 0000322418 scopus 로고
    • (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840.
    • (1990) J. Org. Chem. , vol.55 , pp. 6236
    • Chen, C.-Y.1    Hart, D.J.2
  • 8
    • 0027200915 scopus 로고
    • (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840.
    • (1993) J. Org. Chem. , vol.58 , pp. 3840
    • Chen, C.-Y.1    Hart, D.J.2
  • 15
    • 0029956640 scopus 로고    scopus 로고
    • (h) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Kinoshita, A.; Mon, M. J. Org. Chem. Heterocycles 1997, 46 287. See also: Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1.
    • (1996) J. Org. Chem. , vol.61 , pp. 8356
    • Kinoshita, A.1    Mori, M.2
  • 16
    • 13044276957 scopus 로고    scopus 로고
    • (h) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Kinoshita, A.; Mon, M. J. Org. Chem. Heterocycles 1997, 46 287. See also: Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1.
    • (1997) J. Org. Chem. Heterocycles , vol.46 , pp. 287
    • Kinoshita, A.1    Mon, M.2
  • 17
    • 0032514162 scopus 로고    scopus 로고
    • (h) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Kinoshita, A.; Mon, M. J. Org. Chem. Heterocycles 1997, 46 287. See also: Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1.
    • (1998) J. Mol. Catal. A: Chem. , vol.133 , pp. 1
    • Ivin, K.J.1
  • 24
    • 0343380753 scopus 로고    scopus 로고
    • Unless otherwise indicated all structures refer to racemic compounds
    • (o) Unless otherwise indicated all structures refer to racemic compounds.
  • 25
    • 0000820984 scopus 로고
    • Pearson, W. H., Ed.; Jai Press Inc.: Greenwich, CT, and references therein
    • (a) Jacobi, P. A. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; Jai Press Inc.: Greenwich, CT, 1992; Vol. II, pp 251-98 and references therein.
    • (1992) Advances in Heterocyclic Natural Product Synthesis , vol.2 , pp. 251-298
    • Jacobi, P.A.1
  • 28
    • 0343816438 scopus 로고    scopus 로고
    • note
    • 6b
  • 34
    • 0025329854 scopus 로고
    • See, for example: (a) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401. (b) Thaning, M.; Wistrand, L.-G. J. Org. Chem. 1990, 55, 1406. (c) Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949. (d) Keinan, E.; Peretz, M. J. Org. Chem. 1983, 48, 5302.
    • (1990) J. Org. Chem. , vol.55 , pp. 1406
    • Thaning, M.1    Wistrand, L.-G.2
  • 35
    • 0025121014 scopus 로고
    • See, for example: (a) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401. (b) Thaning, M.; Wistrand, L.-G. J. Org. Chem. 1990, 55, 1406. (c) Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949. (d) Keinan, E.; Peretz, M. J. Org. Chem. 1983, 48, 5302.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4949
    • Bernardi, A.1    Micheli, F.2    Potenza, D.3    Scolastico, C.4    Villa, R.5
  • 36
    • 5244243008 scopus 로고
    • See, for example: (a) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401. (b) Thaning, M.; Wistrand, L.-G. J. Org. Chem. 1990, 55, 1406. (c) Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949. (d) Keinan, E.; Peretz, M. J. Org. Chem. 1983, 48, 5302.
    • (1983) J. Org. Chem. , vol.48 , pp. 5302
    • Keinan, E.1    Peretz, M.2
  • 37
    • 0342945292 scopus 로고    scopus 로고
    • note
    • 3SnOMe, and others.
  • 38
    • 0343380750 scopus 로고    scopus 로고
    • note
    • 2O, methyl ester 29 was cleanly converted to butenolide 28.
  • 39
    • 0342511140 scopus 로고    scopus 로고
    • note
    • (b) We are grateful to Dr. Victor G. Young, of The University of Minnesota, for carrying out the X-ray analysis of 30.
  • 40
    • 0342511141 scopus 로고    scopus 로고
    • note
    • (a) One possible source of oxidant is trace amounts of air in the reaction mixture. Under 1 atm of air 17 undergoes rapid decomposition in refluxing diethylbenzene (182°C).
  • 41
    • 0342945291 scopus 로고    scopus 로고
    • note
    • 3 reference electrode. We gratefully acknowledge Mr. John Porter and Professor Albeit Fry, of Wesleyan University, for assistance in carrying out these experiments. Helpful discussions with Professor Kevin Moeller, of Washington University, St. Louis, are also acknowledged.
  • 44
    • 0343380748 scopus 로고    scopus 로고
    • note
    • 5a
  • 47
    • 0342945290 scopus 로고    scopus 로고
    • note
    • (c) During the course of this work, Kinoshita and Mori reported an independent synthesis of (-)-1 employing butenolide (-)-12b (ref 4h). These authors reported a single product from the reduction of (-)-12b to give (-)-1. In our hands this reduction consistently produced an ∼5:1 mixture of 1 and 34.
  • 48
    • 0343380747 scopus 로고    scopus 로고
    • note
    • We are grateful to Professor David R. Williams, of Indiana University, for providing us with NMR, IR. and mass spectra of authentic (-)-1.
  • 57
    • 0343816433 scopus 로고    scopus 로고
    • note
    • 21c among others.
  • 68
    • 0343816431 scopus 로고    scopus 로고
    • note
    • (a) Financial support of this work by NSF Grant No. CHE-9424476 is gratefully acknowledged.
  • 69
    • 0342511136 scopus 로고    scopus 로고
    • note
    • (b) Additional spectral and analytical data are available in the Supporting Information section of ref 4i.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.