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Volumn 73, Issue 8, 2008, Pages 3078-3087

Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR AGENTS; CYCLOPROPYL GROUP; OTTELIONE; SELECTIVE RING CLOSING METATHESIS;

EID: 42149117901     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702635t     Document Type: Article
Times cited : (26)

References (72)
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    • (b) Dechaine, J. L.; Lewis, H. J.; Ayyad, S.-E. N.; Hoye, T. R.; Sreerama, L. Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003.
  • 10
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    • The dienone system of the otteliones is very rare. For examples, see: a
    • The dienone system of the otteliones is very rare. For examples, see: (a) Birch, A. J. Proc R. Soc. N. S. W. 1949, 83, 245-250.
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    • Dienone 6 underwent both 1,4- and 1,6-addition with cuprates: Wild, H. J. Org. Chem. 1994, 59, 2748-2761.
    • Dienone 6 underwent both 1,4- and 1,6-addition with cuprates: Wild, H. J. Org. Chem. 1994, 59, 2748-2761.
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    • For other synthetic work, see: (a) Hanson, G. H.; Hoye, T. R.; Burke, S. D. Abstracts of Papers, 234th ACS National Meeting, Boston, MA, August 19-23, 2007.
    • For other synthetic work, see: (a) Hanson, G. H.; Hoye, T. R.; Burke, S. D. Abstracts of Papers, 234th ACS National Meeting, Boston, MA, August 19-23, 2007.
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    • Ph.D. Thesis, University of Minnesota, Diss. Abstr. Int. B
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    • Ref 7b
    • (c) Ref 7b.
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    • Ph.D. Thesis, University of Minnesota, Diss. Abstr. Int. B
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    • Ref 6
    • (e) Ref 6.
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    • Preliminary communication: Clive, D. L. J.; Liu, D. Tetrahedron Lett. 2005, 46, 5305-5307.
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    • Prepared from lithium 2-thienylcyanocuprate and 2-lithio-1,3-butadiene, which was generated by the literature route: (a) Brown, P. A.; Jenkins, P. R. J. Chem. Soc., Perkin Trans 1 1986, 1129-1131.
    • Prepared from lithium 2-thienylcyanocuprate and 2-lithio-1,3-butadiene, which was generated by the literature route: (a) Brown, P. A.; Jenkins, P. R. J. Chem. Soc., Perkin Trans 1 1986, 1129-1131.
  • 34
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    • 2-Lithio-1,3-butadiene is also available from 2-(tributylstannyl)-1,3- butadiene: Wada, E.; Kanemasa, S.; Fujiwara, I.; Tsuge, O. Bull. Chem. Soc. Jpn. 1985, 58, 1942-1945.
    • 2-Lithio-1,3-butadiene is also available from 2-(tributylstannyl)-1,3- butadiene: Wada, E.; Kanemasa, S.; Fujiwara, I.; Tsuge, O. Bull. Chem. Soc. Jpn. 1985, 58, 1942-1945.
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    • Preliminary communication: Clive, D. L. J.; Liu, D. Angew. Chem., Int. Ed. 2007, 46, 3738-3740.
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    • We prepared the required phosphorus reagent using a Z/E mixture of 1,3-dichloro-1-propenes and obtained a C(6) epimeric mixture of cyclopropanes that, upon ozonolysis, gave an epimeric mixture of acids. The derived ethyl esters were separated to afford ester 50.
    • We prepared the required phosphorus reagent using a Z/E mixture of 1,3-dichloro-1-propenes and obtained a C(6) epimeric mixture of cyclopropanes that, upon ozonolysis, gave an epimeric mixture of acids. The derived ethyl esters were separated to afford ester 50.
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    • Most of the sequence (51 → 56) turned out to be the same as that used previously by others: (a) Smith, A. B., III; Han, Q.; Breslin, P. A. S.; Beuchamp, G. K. Org. Lett. 2005, 7, 5075-5078.
    • Most of the sequence (51 → 56) turned out to be the same as that used previously by others: (a) Smith, A. B., III; Han, Q.; Breslin, P. A. S.; Beuchamp, G. K. Org. Lett. 2005, 7, 5075-5078.
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    • See Supporting Information for a summary chart of the two other routes we examined
    • See Supporting Information for a summary chart of the two other routes we examined.
  • 66
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    • For related opening of cyclopropyl ketones, see: a
    • For related opening of cyclopropyl ketones, see: (a) Beerli, R.; Brunner, E. J.; Borschberg, H.-J. Tetrahedron Lett. 1992, 33, 6449-6452.
    • (1992) Tetrahedron Lett , vol.33 , pp. 6449-6452
    • Beerli, R.1    Brunner, E.J.2    Borschberg, H.-J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.