Cyclohexenone Annelation by Alkylidene C−H Insertion: Synthesis of Oxo-T-cadinol

Autor:	C. Nicholas Hodge, Thomas E. Christos, Douglass F. Taber and
Rok vydání:	1996
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Allyl bromide chemistry Diazomethane Cyclohexenone Organic Chemistry Cyclopentene Aldol condensation Methylene Carbene Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 61:2081-2084
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo951949k
Popis:	A new procedure for cyclohexenone annelation has been developed. Thus, alkylation of 4-isopropylcyclohexanone with allyl bromide gives, over several steps, ketone 8. Exposure to (trimethylsilyl)diazomethane and MeLi smoothly cyclized 8 to the cyclopentene 9 by insertion of the intermediate alkylidene carbene into the unactivated methylene CH. On debenzylation, ozonolysis, and subsequent aldol condensation, 9 is transformed into oxo-T-cadinol (1).
Databáze:	OpenAIRE
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