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Volumn 47, Issue 35, 2008, Pages 6650-6653

Rapid construction of the cortistatin pentacyclic core

Author keywords

Alkaloids; Angiogenesis; Cycloisomerization; Enynes; Oxidative dearomatization

Indexed keywords

ALKALOIDS; ANGIOGENESIS; CYCLOISOMERIZATION; ENYNES; OXIDATIVE DEAROMATIZATION;

EID: 52449126825     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802203     Document Type: Article
Times cited : (71)

References (37)
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    • During the review of this manuscript, an elegant semi-synthesis of cortistatin A was reported by Baran and co-workers, see
    • During the review of this manuscript, an elegant semi-synthesis of cortistatin A was reported by Baran and co-workers, see: R. A. Shenvi, C. A. Guerrero, J. Shi, C.-C. Li, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 7241-7243.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 7241-7243
    • Shenvi, R.A.1    Guerrero, C.A.2    Shi, J.3    Li, C.-C.4    Baran, P.S.5
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    • Ed, R. H. Thomson, 2nd ed, Blackie, New York, Chapter 4
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    • For details, see the Supporting Information
    • For details, see the Supporting Information.
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    • For the synthesis of 20, see the Supporting Information.
    • For the synthesis of 20, see the Supporting Information.
  • 24
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    • Angew. Chem. Int. Ed. 2008, 47, 4268-4315;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4268-4315
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    • For a related diene hydrogenation using diimide, see
    • For a related diene hydrogenation using diimide, see: X. Li, R. E. Kyne, T. V. Ovaska, Org. Lett. 2006, 8, 5153-5156.
    • (2006) Org. Lett , vol.8 , pp. 5153-5156
    • Li, X.1    Kyne, R.E.2    Ovaska, T.V.3
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    • The relative configuration of epoxides 29 a and 29b was inferred from the assignment of pentacycle 31.
    • The relative configuration of epoxides 29 a and 29b was inferred from the assignment of pentacycle 31.
  • 31
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    • The mechanism of this PMB cleavage is under active investigation and will be reported in due course. The success of this reaction may be dependant on the presence of adventitious O2 for oxidation of the lithiated benzylic carbon of the PMB ether. For an example of an organolithium/O 2-mediated cleavage of a PMB amide, see: R. M. Williams, T. Glinka, E. Kwast, H. Coffman, J. K. Stille, J. Am. Chem. Soc. 1990, 112, 808-821
    • 2-mediated cleavage of a PMB amide, see: R. M. Williams, T. Glinka, E. Kwast, H. Coffman, J. K. Stille, J. Am. Chem. Soc. 1990, 112, 808-821.
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    • Attempted epoxidation of the intermediate phenol led to clean epoxide formation as judged by TLC analysis, but only decomposition products were obtained following a standard workup
    • Attempted epoxidation of the intermediate phenol led to clean epoxide formation as judged by TLC analysis, but only decomposition products were obtained following a standard workup.
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    • 3, it is accompanied by the formation of decomposition products. (Chemical Equation Presented)
    • 3, it is accompanied by the formation of decomposition products. (Chemical Equation Presented)
  • 37
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    • After online publication of our manuscript, we became aware of a relevant manuscript: M. Dai, S. J. Danishefsky, Heterocycles 2008, DOI: COM-08-S(F)6.
    • After online publication of our manuscript, we became aware of a relevant manuscript: M. Dai, S. J. Danishefsky, Heterocycles 2008, DOI: COM-08-S(F)6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.