Reactions of cyclohexadienes. Part VIII. Stereoselective and nonstereoselective syntheses of (±)-juvabione

Autor:	Arthur J. Birch, P. L. Macdonald, V.H. Powell
Rok vydání:	1970
Předmět:	chemistry.chemical_compound Natural product chemistry Stereochemistry Yield (chemistry) Organic Chemistry Cyclohexadienes Diastereomer Organic chemistry Stereoselectivity Juvabione Adduct
Zdroj:	J. Chem. Soc. C. :1469-1476
ISSN:	0022-4952
DOI:	10.1039/j39700001469
Popis:	Diels–Alder adducts from readily available dihydroanisoles and several αβ-unsaturated ketones have previously been shown to undergo acid-catalysed ring-opening to yield 4-substituted cyclohexenones. As the first example of the utility of this general process in natural product synthesis, a simple and efficient synthesis of (±)-juvabione diastereoisomers has been carried out. The synthesis was extended to yield (±)-juvabione in a stereoselective manner and confirms the recently revised stereochemistry of (±)-juvabione.
Databáze:	OpenAIRE
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