An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate

Autor:	Ji-In Kim Almstead, Benoit Ledoussal, Thomas P. Demuth
Rok vydání:	1998
Předmět:	Allyl bromide Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Robinson annulation Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Diterpene Carbonylation Methyl group
Zdroj:	Tetrahedron: Asymmetry. 9:3179-3183
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(98)00349-8
Popis:	A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C8 position. A palladium-mediated carbonylation reaction was employed to generate the key α,β-unsaturated dialdehyde.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::731106065452be6a769304b90dea0469 https://doi.org/10.1016/s0957-4166(98)00349-8 Zobrazit plný text záznamu Full Text from ScienceDirect