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Volumn 62, Issue 15, 1997, Pages 5069-5073

Cyclopropanation/reduction of a 3,4-disubstituted 2(5H)-furanone: A model for C-8 methylation at the taxane BC ring juncture

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 10 OXABICYCLO[6.3.0]UNDECAN 9 ONE; 10 OXA[6.3.1]PROPELLAN 9 ONE; 4,5,6,7,8,9 HEXAHYDROCYCLOOCTA[C]FURAN 1(3H) ONE; AMMONIA; CYCLOPROPANE; DEUTERIUM; DIMETHYL SULFOXIDE; FURANONE DERIVATIVE; LITHIUM; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030790368     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970564u     Document Type: Article
Times cited : (14)

References (43)
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    • note
    • We believe that this modest isolated yield is a function of the product isolation efficiency.
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    • In retrospect, it is not surprising that the lactone functionality was reduced. Treatment of β-keto ester i with lithium in liquid ammonia is known to afford hydrindanone ii and decalin iii, where cyclopropane reduction is accompanied by reduction of the ester group (ref 21). (Matrix Presented)
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    • This resonance was not reported in reference 5; instead, a signal at δ 150.0 was cited.
  • 43
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    • note
    • 2 carbon resonance was not observable above the spectral base line.


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