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Volumn 73, Issue 22, 2008, Pages 8929-8941

[2,3]-Sigmatropic rearrangements of 3-sulfinyl dihydropyrans: application to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; TOLUENE;

EID: 56449100516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015709     Document Type: Article
Times cited : (30)

References (76)
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    • Recent examples: (a) Fernández de la Pradilla, R.; Lwoff, N. Tetrahedron Lett. 2008, 49, 4167-4169.
    • Recent examples: (a) Fernández de la Pradilla, R.; Lwoff, N. Tetrahedron Lett. 2008, 49, 4167-4169.
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    • For an example retaining the sulfur atom see: f
    • For an example retaining the sulfur atom see: (f) Satoh, T.; Miyagawa, T. Tetrahedron Lett. 2006, 47, 1981-1983.
    • (2006) Tetrahedron Lett , vol.47 , pp. 1981-1983
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    • The conformation around the sulfur atom could also be influenced by coordination of the sulfinyl and ring oxygens with the solvent thus increasing the steric bulk around those atoms. See: (a) McNelis, B. J, Sternbach, D. D, MacPhail, A. T. Tetrahedron 1994, 50, 6767-6782
    • The conformation around the sulfur atom could also be influenced by coordination of the sulfinyl and ring oxygens with the solvent thus increasing the steric bulk around those atoms. See: (a) McNelis, B. J.; Sternbach, D. D.; MacPhail, A. T. Tetrahedron 1994, 50, 6767-6782.
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    • For a review on the determination of absolute configuration by NMR, see: b
    • For a review on the determination of absolute configuration by NMR, see: (b) Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17-118.
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    • Stereochemistry of vinyl sulfoxide could not be determined
    • Stereochemistry of vinyl sulfoxide could not be determined.
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    • and references therein. Bicyclic amidines DBU and DBN have been termed as nonnucleophilic strong bases but numerous examples have been reported which demonstrate that they can also act as nucleophiles. For examples, see
    • Bicyclic amidines DBU and DBN have been termed as "nonnucleophilic strong bases" but numerous examples have been reported which demonstrate that they can also act as nucleophiles. For examples, see: Baidya, M.; Mayr, H. Chem. Commun 2008, 1792-1794, and references therein.
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    • The reaction mixture had to be carefully degassed before closing the system and heating at 70°C for the yields to be reproducible.
    • The reaction mixture had to be carefully degassed before closing the system and heating at 70°C for the yields to be reproducible.
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    • Total syntheses: (a) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2000, 2, 635-638.
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    • Partial and formal syntheses: (g) Naito, T.; Nair, J. S.; Nishiki, A.; Yamashita, K.; Kiguchi, T. Heterocycles 2000, 53, 2611-2615.
    • Partial and formal syntheses: (g) Naito, T.; Nair, J. S.; Nishiki, A.; Yamashita, K.; Kiguchi, T. Heterocycles 2000, 53, 2611-2615.
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    • See also ref 6a
    • (l) See also ref 6a.
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    • Related studies: (m) Lygo, B.; Slack, D.; Wilson, C. Tetrahedron Lett. 2005, 46, 6629-6632.
    • Related studies: (m) Lygo, B.; Slack, D.; Wilson, C. Tetrahedron Lett. 2005, 46, 6629-6632.
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    • (c) Hwu, J. R. J. Org. Chem. 1983, 48, 4432-4433.
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    • MS thesis, Universidad Complutense de Madrid, September
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    • The tethered aminohydroxylation was carried out in small scale and it has been previously reported that under these conditions the yields vary unpredictably from 4 to 40, See: Curtis, K. L, Fawcett, J, Handa, S. Tetrahedron Lett. 2005, 46, 5297-5300
    • The tethered aminohydroxylation was carried out in small scale and it has been previously reported that under these conditions the yields vary unpredictably from 4 to 40%. See: Curtis, K. L.; Fawcett, J.; Handa, S. Tetrahedron Lett. 2005, 46, 5297-5300.
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    • Since the exploratory study with a TBDMS silyl ether was carried out at small scale, and the sequence was not completed, the intermediates could not be fully characterized
    • Since the exploratory study with a TBDMS silyl ether was carried out at small scale, and the sequence was not completed, the intermediates could not be fully characterized.
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    • 2 led to complex reaction mixtures, where only traces of the desired product could be identified.
    • 2 led to complex reaction mixtures, where only traces of the desired product could be identified.


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