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Volumn 75, Issue 23, 2010, Pages 8258-8270

Nicholas reactions in the construction of cyclohepta[ de ]naphthalenes and cyclohepta[de]naphthalenones. The total synthesis of microstegiol

Author keywords

[No Author keywords available]

Indexed keywords

DEPROTECTION; METHYL GROUP; NICHOLAS REACTIONS; RING CLOSING METATHESIS; RING CLOSURES; TAUTOMERIZATIONS; TOTAL SYNTHESIS;

EID: 78650288787     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102127q     Document Type: Article
Times cited : (26)

References (84)
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    • addition, some homologues, such as the hypocrellins, have seen recent synthetic attention
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    • For reviews covering Nicholas reactions in part, see ref 9 and the following:; J. Chem. Soc., Perkin Trans. 1 2000, 1657-1668
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    • For γ-carbonyl cation equivalents by way of carbonyl-substituted cyclopropanes, see: Lifchits, O.; Alberico, D.; Zakharian, I.; Charette, A. B. J. Org. Chem. 2008, 73, 6838 and references cited therein
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    • 2 in Nicholas reactions for substrates possessing Lewis basic groups has been observed in our group previously
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    • Attempts to subject 41 to initial acetylation, in order to give an expedited route to 44, were not selective for protection of the C-2 alcohol
    • Attempts to subject 41 to initial acetylation, in order to give an expedited route to 44, were not selective for protection of the C-2 alcohol.


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