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Volumn 73, Issue 1, 2008, Pages 142-150

Total synthesis of (-)-hennoxazole A

Author keywords

[No Author keywords available]

Indexed keywords

BISOXAZOLE SYSTEM; CYCLODEHYDRATION; DOUBLE BOND; PYRAN-BASED RING SYSTEM;

EID: 37549023756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7018015     Document Type: Article
Times cited : (35)

References (84)
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    • Several other natural products containing more than two contiguous oxazoles are also known, including the mycalolides, ulapualides, and kabiramides, which have three directly linked oxazole rings, and telomestatin, which has seven. For a review of the syntheses of oxazole-containing natural products, see: a
    • Several other natural products containing more than two contiguous oxazoles are also known, including the mycalolides, ulapualides, and kabiramides - which have three directly linked oxazole rings - and telomestatin, which has seven. For a review of the syntheses of oxazole-containing natural products, see: (a) Yeh, V. S. C. Tetrahedron 2004, 60, 11995-12042.
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    • For a lead reference on telomestatin, see: d
    • For a lead reference on telomestatin, see: (d) Doi, T.; Yoshida, M.; Shin-ya, K.; Takahashi, T. Org. Lett. 2006, 8, 4165-4167.
    • (2006) Org. Lett , vol.8 , pp. 4165-4167
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  • 10
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    • (b) Wipf, P.; Lim, S. Chimia 1996, 50, 157-167.
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    • For other synthetic studies see: a
    • For other synthetic studies see: (a) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415-416.
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    • Portions of this work have been reported in previous papers: (a) Smith, T. E.; Balskus, E. P. Heterocycles 2002, 57, 1219-1225.
    • Portions of this work have been reported in previous papers: (a) Smith, T. E.; Balskus, E. P. Heterocycles 2002, 57, 1219-1225.
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    • For a review of the uses of oxazoles as protected carboxylate equivalents see: a
    • For a review of the uses of oxazoles as protected carboxylate equivalents see: (a) Wasserman, H. H.; McCarthy, K. E.; Prowse, K. S. Chem. Rev. 1986, 86, 845-856.
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    • For a review of oxazole metalation see: f
    • For a review of oxazole metalation see: (f) Iddon, B. Heterocycles 1994, 37, 1321-1346.
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    • For the original solution to this problem see: a
    • For the original solution to this problem see: (a) Evans, D. A.; Cee, V. J.; Smith, T. E.; Santiago, K. J. Org. Lett. 1999, 1, 87-90.
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  • 44
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    • For subsequent applications of this method to the synthesis of phorboxazoles see: d
    • For subsequent applications of this method to the synthesis of phorboxazoles see: (d) González, M. A.; Pattenden G. Angew. Chem., Int. Ed. 2003, 42, 1255-1258.
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    • For further investigation of this effect see
    • For further investigation of this effect see: Smith, T. E.; Mourad, M. S.; Velander, A. J. Heterocycles 2002, 57, 1211-1217.
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    • Williams carried out semiempirical calculations also suggesting that the ring-lithiated intermediate was thermodynamically favored due to chelation with the adjacent oxazole nitrogen. See ref 15
    • Williams carried out semiempirical calculations also suggesting that the ring-lithiated intermediate was thermodynamically favored due to chelation with the adjacent oxazole nitrogen. See ref 15.
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    • 5 was one approach to solving "the oxazole problem" in virginiamycin: (a) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1983, 24, 4391-4392.
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    • 1H NMR and GC-MS analysis.
    • 1H NMR and GC-MS analysis.
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    • Stereochemical erosion in the syn-diastereomer of this type of [2,3]-Wittig rearrangment has been observed previously: Tsubuki, M.; Kamata, T.; Nakatani, M.; Yamazaki, K.; Matsui, T.; Honda, T. Tetrahedron: Asymmetry 2000, 11, 4725-4736.
    • Stereochemical erosion in the syn-diastereomer of this type of [2,3]-Wittig rearrangment has been observed previously: Tsubuki, M.; Kamata, T.; Nakatani, M.; Yamazaki, K.; Matsui, T.; Honda, T. Tetrahedron: Asymmetry 2000, 11, 4725-4736.
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    • For an improved preparation of the (Z)-pentenyl boronate reagent, see: (b) Bahnck, K. B.; Rychnovsky, S. D. Chem. Commun. 2006, 2388-2390.
    • For an improved preparation of the (Z)-pentenyl boronate reagent, see: (b) Bahnck, K. B.; Rychnovsky, S. D. Chem. Commun. 2006, 2388-2390.
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    • Homoallylic alcohol 37 is also an intermediate in Williams's synthesis, but required six steps to prepare from 7.
    • Homoallylic alcohol 37 is also an intermediate in Williams's synthesis, but required six steps to prepare from 7.
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    • As an additional benefit, product 47b could be reduced to the corresponding aldehyde in a single step using DIBAL-H, whereas attempted reduction of 47a and 48a always gave significant amounts of overreduction to the primary alcohols, which would necessitate a two-step reduction/oxidation sequence.
    • As an additional benefit, product 47b could be reduced to the corresponding aldehyde in a single step using DIBAL-H, whereas attempted reduction of 47a and 48a always gave significant amounts of overreduction to the primary alcohols, which would necessitate a two-step reduction/oxidation sequence.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.