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Volumn 37, Issue 14, 1996, Pages 2463-2466

Formation of heterocycles by the mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALPHA SKYTANTHINE; TERPENE; UNCLASSIFIED DRUG;

EID: 0029868659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00319-X     Document Type: Article
Times cited : (78)

References (24)
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    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 2
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    • The Mitsunobu reaction
    • Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York
    • Reviews: Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. L. The Mitsunobu Reaction, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656.
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    • Hughes, D.L.1
  • 4
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    • Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542. Itô, S; Tsunoda, T. Pure & Appl. Chem. 1994, 66, 2071-2074.
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    • Itô, S.1    Tsunoda, T.2
  • 9
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    • Intermolecular ether formation with traditional Mitsunobu reagents seems to proceed only with more acidic O-nucleophiles, such as phenols, enols, and perfluorocarbinols. Ref. 1 and also Cho, H.-S.; Yu, J.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 8354-8355.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8354-8355
    • Cho, H.-S.1    Yu, J.2    Falck, J.R.3
  • 11
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    • Intramolecular ether formation is described in ref. 1, and also e.g. Carlock, J. T.; Mack, M. P. Tetrahedron Lett. 1978, 5153-5156.
    • (1978) Tetrahedron Lett. , pp. 5153-5156
    • Carlock, J.T.1    Mack, M.P.2
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    • Intramolecular amine formation, see e.g. a. Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496.
    • (1994) J. Org. Chem. , vol.59 , pp. 2487-2496
    • Chen, Y.1    Vogel, P.2
  • 13
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    • and the references cited therein
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    • Bernotas, R.C.1    Cube, R.C.2
  • 14
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    • Recently, the use of our azo reagents in inter-and intramolecular ether formation has been described. Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385. Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett.. 1994, 35, 5997-6000. Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. Tetrahedron Lett. 1995, 36, 3165-3168. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
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  • 15
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    • Recently, the use of our azo reagents in inter-and intramolecular ether formation has been described. Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385. Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett.. 1994, 35, 5997-6000. Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. Tetrahedron Lett. 1995, 36, 3165-3168. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4585-4586
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    • Recently, the use of our azo reagents in inter-and intramolecular ether formation has been described. Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385. Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett.. 1994, 35, 5997-6000. Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. Tetrahedron Lett. 1995, 36, 3165-3168. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5997-6000
    • Falck, J.R.1    Yu, J.2    Cho, H.-S.3
  • 17
    • 0028953208 scopus 로고
    • Recently, the use of our azo reagents in inter-and intramolecular ether formation has been described. Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385. Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett.. 1994, 35, 5997-6000. Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. Tetrahedron Lett. 1995, 36, 3165-3168. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3165-3168
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  • 18
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    • Recently, the use of our azo reagents in inter-and intramolecular ether formation has been described. Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385. Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett.. 1994, 35, 5997-6000. Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. Tetrahedron Lett. 1995, 36, 3165-3168. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3789-3792
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    • Stereochemistry of the products was confirmed by direct comparison with authentic samples. Griffiths, D. V.; Wilcox, G. J Chem. Soc., Parkin Trans. II 1988, 431-436. Aslani-Shotorbani, G.; Buchanan, J. G.; Edgar, A. R.; Shanks, C. T.; Williams, G. C. J. Chem. Soc., Parkin Trans. I 1981, 2267-2272.
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    • Griffiths, D.V.1    Wilcox, G.2


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