- Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology
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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.
- Yao, Sulan,Johannsen, Mogens,Hazell, Rita G.,J?rgensen, Karl Anker
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p. 118 - 121
(2007/10/03)
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- Carotenoids and Degraded Carotenoids, VIII. Synthesis of (+)-Dihydroactinidiolide, (+)- and (-)-Actinidiolide, (+)- and (-)-Loliolide as well as (+)- and (-)-Epiloliolide
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Enantiomerically pure (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (1) was efficiently converted into four degraded lactonic carotenoids: (S)-dihydroactinidiolide (5), (S)-actinidiolide (9), (6S,7aR)-loliolide (11) and (6S,7aS)-epiloliolide (12). (R)-Actinidioli
- Mori, Kenji,Khlebnikov, Vladimir
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- Oxidation of Enol Silyl Ethers: Preparation of Aeginetolide, Dihydroactinidiolide, and Actinidiolide
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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.
- Rubottom, George M.,Juve, Henrik D.
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p. 422 - 425
(2007/10/02)
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