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Volumn 9, Issue 20, 2007, Pages 3941-3943

A [3 + 3] annelation approach to (+)-rhopaloic acid B

Author keywords

[No Author keywords available]

Indexed keywords

ACID; EPOXIDE; PYRAN DERIVATIVE; RHOPALOIC ACID B; UNCLASSIFIED DRUG;

EID: 35048847899     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701553j     Document Type: Article
Times cited : (20)

References (32)
  • 8
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    • For a recent enantioselective synthesis of related hippospongic acid A and lead references see
    • For a recent enantioselective synthesis of related hippospongic acid A and lead references see: Trost, B. M.; Machacek, M. R.; Tsui, H. C. J. Am. Chem. Soc. 2005, 127, 7014.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 7014
    • Trost, B.M.1    Machacek, M.R.2    Tsui, H.C.3
  • 9
    • 18444378413 scopus 로고    scopus 로고
    • For reviews of [3 + 3] approaches to heterocycle systems see: (a) Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 1349.
    • For reviews of [3 + 3] approaches to heterocycle systems see: (a) Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 1349.
  • 18
    • 84985502069 scopus 로고
    • For a review of Pd-TMM cycloadditions see
    • For a review of Pd-TMM cycloadditions see: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
    • (1986) Angew. Chem., Int. Ed. Engl , vol.25 , pp. 1
    • Trost, B.M.1
  • 19
    • 0001081027 scopus 로고    scopus 로고
    • For [3 + 3] approaches to pyrans see: (a) Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888.
    • For [3 + 3] approaches to pyrans see: (a) Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888.
  • 26
    • 0026447774 scopus 로고    scopus 로고
    • Addition of a related Grignard reagent to epoxides has been shown to produce pyrans. However, this reagent is prepared in two steps in modest yield. Moreover, the Grignard formation was found to be highly prone to Wurtz coupling in our hands, van der Louw, J.; van der Baan, J. L.; Out, G. J. J.; de Kanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron 1992, 48, 9901.
    • Addition of a related Grignard reagent to epoxides has been shown to produce pyrans. However, this reagent is prepared in two steps in modest yield. Moreover, the Grignard formation was found to be highly prone to Wurtz coupling in our hands, van der Louw, J.; van der Baan, J. L.; Out, G. J. J.; de Kanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron 1992, 48, 9901.
  • 27
    • 11844292026 scopus 로고    scopus 로고
    • For a recent example of transition metal-catalyzed cyclodehydration and lead references see
    • For a recent example of transition metal-catalyzed cyclodehydration and lead references see: Shibata, T.; Fujiwara, R.; Ueno, Y. Synlett 2005, 152.
    • (2005) Synlett , pp. 152
    • Shibata, T.1    Fujiwara, R.2    Ueno, Y.3
  • 31
    • 0000526264 scopus 로고    scopus 로고
    • This result was obtained by using aged catalyst. The employment of freshly prepared Wilkinson's catalyst resulted in a significantly slower reaction, albeit with better levels of selectivity. For a mechanistic study and lead references see: Evans, D. A, Fu, G. C, Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679
    • This result was obtained by using aged catalyst. The employment of freshly prepared Wilkinson's catalyst resulted in a significantly slower reaction, albeit with better levels of selectivity. For a mechanistic study and lead references see: Evans, D. A.; Fu, G. C.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.