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Volumn 46, Issue 48, 2007, Pages 9211-9214

Total synthesis and stereochemical reassignment of (+)-neopeltolide

Author keywords

Annulation; Antitumor agents; Macrolides; Natural products; Total synthesis

Indexed keywords

ANTITUMOR AGENTS; MACROLIDES; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 37349010312     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704122     Document Type: Article
Times cited : (96)

References (44)
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    • For syntheses of the leucascandrolide A macrolide, see j
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    • Other reports of leucascandrolide A fragments include: p M. T. Crimmins, C. A. Carroll, B. W. King, Org. Lett. 2000, 2, 597-599;
    • Other reports of leucascandrolide A fragments include: p) M. T. Crimmins, C. A. Carroll, B. W. King, Org. Lett. 2000, 2, 597-599;
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    • 13C NMR spectra of these compounds, see the Supporting Information. These spectroscopic differences, along with identical mass spectroscopy data and fragmentation patterns for both samples, suggested a possible misassignment (data were kindly provided by Dr A. E. Wright).
    • 13C NMR spectra of these compounds, see the Supporting Information. These spectroscopic differences, along with identical mass spectroscopy data and fragmentation patterns for both samples, suggested a possible misassignment (data were kindly provided by Dr A. E. Wright).
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    • Compound 7 was synthesized in the same way as its enantiomer, see N. Holub, J. Neidhofer, S. Blechert, Org. Lett. 2005, 7, 1227-1229.
    • Compound 7 was synthesized in the same way as its enantiomer, see N. Holub, J. Neidhofer, S. Blechert, Org. Lett. 2005, 7, 1227-1229.
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    • Methyl (R)-(+)-3-methylglutarate is available from Sigma-Aldrich Co. (Catalog number 380466). Alternatively, it can be prepared through enzymatic desymmetrization of racemic dimethyl 3-methylglutarate with porcine liver esterase, see L. K. P. Lam, R. A. H. F. Hui, J. B. Jones, J. Org. Chem. 1986, 51, 2047-2050.
    • Methyl (R)-(+)-3-methylglutarate is available from Sigma-Aldrich Co. (Catalog number 380466). Alternatively, it can be prepared through enzymatic desymmetrization of racemic dimethyl 3-methylglutarate with porcine liver esterase, see L. K. P. Lam, R. A. H. F. Hui, J. B. Jones, J. Org. Chem. 1986, 51, 2047-2050.
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    • 13C NMR spectroscopic analysis of the acetonide derived from the diol product obtained after DIBAL-H reduction of the C13 acyl protecting group. S. D. Rychnovsky, B. Rogers, G. Yang, J. Org. Chem. 1993, 58, 3511-3515.
    • 13C NMR spectroscopic analysis of the acetonide derived from the diol product obtained after DIBAL-H reduction of the C13 acyl protecting group. S. D. Rychnovsky, B. Rogers, G. Yang, J. Org. Chem. 1993, 58, 3511-3515.
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    • For preparation of the phosphonoacetic acid, see, and references therein
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    • 13C NMR spectra of 1b and 1a, see the Supporting Information.
    • 13C NMR spectra of 1b and 1a, see the Supporting Information.
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    • Starting from commercially available methyl (R)-(+)-3- methylglutarate 9.
    • Starting from commercially available methyl (R)-(+)-3- methylglutarate 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.