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Volumn 52, Issue 45, 1996, Pages 14147-14176

Taxane diterpenes 3: Formation of the eight-membered B-ring by semi-pinacol rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

EID: 0030569280     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00865-4     Document Type: Article
Times cited : (20)

References (25)
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    • 3 ether III, followed by butyl lithium gave IV. So at least an intramolecular addition is feasible. Deprotection of I and conversion of the C-20 alcohol into the ether V, followed by treatment with t-butyl lithium gave the carbenoid cyclopropanation adduct VI (structure by X-ray). The reluctance of the compound I to undergo addition directed our efforts towards examining a semi-pinacol-type rearrangement in the top-half of the bicyclo[5.4.0]undecenone structure. (equation presented)
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    • 14. Treatment of 50 with DBU gave a mixture which contains two unsaturated aldehydes, tentatively assigned the structures VII and VIII. The presence of VIII was indicated by a proton at δ 6.9 (dd); The formation of VIII indicates that the isomerization of the C-3/4 double bond into the C-4/5 position, as suggested in Scheme 5 is feasible, but under basic conditions no ring expansion was observed. (equation presented)


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