17063-17-1Relevant articles and documents
Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology
Yao, Sulan,Johannsen, Mogens,Hazell, Rita G.,J?rgensen, Karl Anker
, p. 118 - 121 (2007/10/03)
The total synthesis of the naturally occurring bicyclic lactones (R)-dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.
Oxidation of Enol Silyl Ethers: Preparation of Aeginetolide, Dihydroactinidiolide, and Actinidiolide
Rubottom, George M.,Juve, Henrik D.
, p. 422 - 425 (2007/10/02)
The preparation of the C11-terpenic lactones aeginetolide (1), dihydroactinidiolide (2), and actinidiolide (3) by using 1,3,3-trimethyl-2-(trimethylsiloxy)cyclohexene (9) as a common precursor is discussed.The key steps in the synthetic route involve the sequential m-chloroperbenzoic acid (MCPBA) oxidation and acetylation of 9 and of the siloxy diene 13 derived from 9.