메뉴 건너뛰기




Volumn 65, Issue 20, 2000, Pages 6293-6306

Total syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (-)-norsecurinine, and phyllanthine

Author keywords

[No Author keywords available]

Indexed keywords

14,15 DIHYDRONORSECURININE; ALKALOID DERIVATIVE; AMIDE; BUTENOLIDE; HYDROXYPROLINE; NITRILE; NORSECURININE; OCTANE; PHYLLANTHINE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

EID: 0034613331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000260z     Document Type: Article
Times cited : (109)

References (62)
  • 1
    • 0011311913 scopus 로고
    • The Securinega Alkaloids
    • Manske, R. H. F., Ed.; Academic Press: New York
    • For excellent reviews, see: (a) Snieckus, V. The Securinega Alkaloids. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 425. (b) Beutler, J. A.; Brubaker, A. N. Drugs Fut. 1987, 12, 957.
    • (1973) The Alkaloids , vol.14 , pp. 425
    • Snieckus, V.1
  • 2
    • 0023549451 scopus 로고
    • For excellent reviews, see: (a) Snieckus, V. The Securinega Alkaloids. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 425. (b) Beutler, J. A.; Brubaker, A. N. Drugs Fut. 1987, 12, 957.
    • (1987) Drugs Fut. , vol.12 , pp. 957
    • Beutler, J.A.1    Brubaker, A.N.2
  • 4
    • 0014259532 scopus 로고
    • Parello, J. Bull. Soc. Chim. Fr. 1968, 1117. Arbain, D.; Birkbeck, A. A.; Byrne, L. T.; Sargent, M. V.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 1 1991, 1863.
    • (1968) Bull. Soc. Chim. Fr. , pp. 1117
    • Parello, J.1
  • 16
    • 13044285433 scopus 로고    scopus 로고
    • (c) Dong, N. Z.; Gu, Z. L.; Chou, W. H.; Kwok, C. Y. Chung Kuo Li Hsueh Pao 1999, 20, 267; Chem Abstr. 1999, 130, 346993n.
    • (1999) Chem Abstr. , vol.130
  • 18
    • 85004374650 scopus 로고
    • Saito, S.; Yoshikawa, H.; Sato, Y.; Nakai, H.; Sugimoto, N.; Horii, Z.; Hanaoka, M.; Tamura, Y. Chem. Pharm. Bull. 1966, 14, 313. See also: Horii, Z.; Imanishi, T.; Tanaka, T.; Mori, I.; Hanaoka, M.; Iwata, C. Chem. Pharm. Bull. 1972, 20, 1768. Horii, Z.; Imanishi, T.; Hanaoka, M.; Iwata, C. Chem. Pharm. Bull. 1972, 20, 1774.
    • (1972) Chem. Pharm. Bull. , vol.20 , pp. 1768
    • Horii, Z.1    Imanishi, T.2    Tanaka, T.3    Mori, I.4    Hanaoka, M.5    Iwata, C.6
  • 19
    • 0039745558 scopus 로고
    • Saito, S.; Yoshikawa, H.; Sato, Y.; Nakai, H.; Sugimoto, N.; Horii, Z.; Hanaoka, M.; Tamura, Y. Chem. Pharm. Bull. 1966, 14, 313. See also: Horii, Z.; Imanishi, T.; Tanaka, T.; Mori, I.; Hanaoka, M.; Iwata, C. Chem. Pharm. Bull. 1972, 20, 1768. Horii, Z.; Imanishi, T.; Hanaoka, M.; Iwata, C. Chem. Pharm. Bull. 1972, 20, 1774.
    • (1972) Chem. Pharm. Bull. , vol.20 , pp. 1774
    • Horii, Z.1    Imanishi, T.2    Hanaoka, M.3    Iwata, C.4
  • 25
    • 0342843378 scopus 로고    scopus 로고
    • note
    • (c) We are grateful to Professor Jacobi for providing spectra of authentic norsecurinine.
  • 28
    • 0018186177 scopus 로고
    • and references cited
    • For studies on the biosynthesis of the Securinega alkaloids, see: Parry, R. J. Bioorg. Chem. 1978, 7, 277 and references cited.
    • (1978) Bioorg. Chem. , vol.7 , pp. 277
    • Parry, R.J.1
  • 29
    • 0029827222 scopus 로고    scopus 로고
    • Preliminary accounts of portions of this research have appeared: (a) Weinreb, S. M. J. Heterocycl. Chem. 1996, 33, 1437. (b) Han, G.; LaPorte, M. G.; Folmer, J. J.; Werner, K. M.; Weinreb, S. M. Angew. Chem., Int. Ed. Engl. 2000, 39, 237.
    • (1996) J. Heterocycl. Chem. , vol.33 , pp. 1437
    • Weinreb, S.M.1
  • 31
    • 0343278166 scopus 로고
    • Ph.D. Thesis, The Pennsylvania State University
    • This work is taken in part from: (a) Folmer, J. J. Ph.D. Thesis, The Pennsylvania State University, 1994. (b) Han, G. Ph.D. Thesis, The Pennsylvania State University, 1997. (c) LaPorte, M. G. Ph.D. Thesis, The Pennsylvania State University, 2000.
    • (1994)
    • Folmer, J.J.1
  • 32
    • 0342843377 scopus 로고    scopus 로고
    • Ph.D. Thesis, The Pennsylvania State University
    • This work is taken in part from: (a) Folmer, J. J. Ph.D. Thesis, The Pennsylvania State University, 1994. (b) Han, G. Ph.D. Thesis, The Pennsylvania State University, 1997. (c) LaPorte, M. G. Ph.D. Thesis, The Pennsylvania State University, 2000.
    • (1997)
    • Han, G.1
  • 33
    • 0343713710 scopus 로고    scopus 로고
    • Ph.D. Thesis, The Pennsylvania State University
    • This work is taken in part from: (a) Folmer, J. J. Ph.D. Thesis, The Pennsylvania State University, 1994. (b) Han, G. Ph.D. Thesis, The Pennsylvania State University, 1997. (c) LaPorte, M. G. Ph.D. Thesis, The Pennsylvania State University, 2000.
    • (2000)
    • LaPorte, M.G.1
  • 39
    • 0342843376 scopus 로고
    • Muller, P.; Gilabert, D. M. Tetrahedron 1988, 44, 1171. Larsen, J.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1992, 1213.
    • (1988) Tetrahedron , vol.44 , pp. 1171
    • Muller, P.1    Gilabert, D.M.2
  • 41
    • 37049104551 scopus 로고
    • This transformation could also be effected, but less conveniently, with diphenylseleninic anhydride: Czarny, M. R. J. Chem. Soc., Chem. Commun. 1976, 81. Czarny, M. R. Synth. Commun. 1976, 6, 285.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 81
    • Czarny, M.R.1
  • 42
    • 0343713706 scopus 로고
    • This transformation could also be effected, but less conveniently, with diphenylseleninic anhydride: Czarny, M. R. J. Chem. Soc., Chem. Commun. 1976, 81. Czarny, M. R. Synth. Commun. 1976, 6, 285.
    • (1976) Synth. Commun. , vol.6 , pp. 285
    • Czarny, M.R.1
  • 44
    • 0003719612 scopus 로고
    • Academic Press: Orlando; Chapter 2
    • For reviews of the imino Diels-Alder reaction, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: Orlando, 1987; Chapter 2. (b) Weinreb, S. M. Heterodienophile Additions to Dienes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 401.
    • (1987) Hetero Diels-Alder Methodology in Organic Synthesis
    • Boger, D.L.1    Weinreb, S.M.2
  • 45
    • 0000730407 scopus 로고
    • Heterodienophile Additions to Dienes
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For reviews of the imino Diels-Alder reaction, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: Orlando, 1987; Chapter 2. (b) Weinreb, S. M. Heterodienophile Additions to Dienes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 401.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 401
    • Weinreb, S.M.1
  • 48
    • 0000340186 scopus 로고
    • For lead references, see: (a) Ishibashi, H.; Nakatani, H.; Iwami, S.; Sato, T.; Nakamura, N.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1989, 1767. (b) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (c) Iwamatsu, S.; Matsubara, K.; Nagashima, H. J. Org. Chem. 1999, 64, 9625.
    • (1993) J. Org. Chem. , vol.58 , pp. 464
    • Nagashima, H.1    Ozaki, N.2    Ishii, M.3    Seki, K.4    Washiyama, M.5    Itoh, K.6
  • 49
    • 0033601284 scopus 로고    scopus 로고
    • For lead references, see: (a) Ishibashi, H.; Nakatani, H.; Iwami, S.; Sato, T.; Nakamura, N.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1989, 1767. (b) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (c) Iwamatsu, S.; Matsubara, K.; Nagashima, H. J. Org. Chem. 1999, 64, 9625.
    • (1999) J. Org. Chem. , vol.64 , pp. 9625
    • Iwamatsu, S.1    Matsubara, K.2    Nagashima, H.3
  • 50
    • 84982395633 scopus 로고
    • Bestmann, H. J.; Sandmeier, D. Chem Ber. 1980, 113, 274. Nickisch, K.; Klose, W.; Bohlmann, F. Chem Ber. 1980, 113, 2038.
    • (1980) Chem Ber. , vol.113 , pp. 274
    • Bestmann, H.J.1    Sandmeier, D.2
  • 52
    • 0342408453 scopus 로고    scopus 로고
    • note
    • We are indebted to Dr. C. J. Easton and J. Kelly (Australian National University) for recording the ORD spectrum of synthetic (+)-14,15-dihydronorsecurinine (8).
  • 57
    • 0342843375 scopus 로고    scopus 로고
    • note
    • A byproduct in this reaction has been tentatively identified as the phenylselenonorsecurinine i. We are uncertain as to the genesis of this compound. (formula presented)
  • 59
    • 0000666915 scopus 로고
    • Miyoshi, N.; Yamamoto, T.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1982, 23, 4813. Watanabe, M.; Awen, B. Z.; Kato, M. J. Org. Chem. 1993, 58, 3923.
    • (1993) J. Org. Chem. , vol.58 , pp. 3923
    • Watanabe, M.1    Awen, B.Z.2    Kato, M.3
  • 61
    • 0342843350 scopus 로고    scopus 로고
    • note
    • Attempted application of this procedure to convert norsecurinine intermediate 46 to enone 48 failed.
  • 62
    • 0343713667 scopus 로고    scopus 로고
    • note
    • Formation of the amine hydrochloride by this procedure was fortuitous but was not planned.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.