- Synthesis of loliolide, actinidiolide, dihydroactinidiolide, and aeginetolide via cerium enolate chemistry
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(Chemical Equation Presented) Loliolide, aeginetolide, actinidiolide, and dihydroactinidiolide were synthesized in racemic form from a single common intermediate, prepared through the 1,2 addition of the cerium enolate of ethyl acetate to 2,6,6-trimethylcylohexenone.
- Eidman, Kirk F.,MacDougall, Brian S.
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p. 9513 - 9516
(2007/10/03)
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- Stereocontrolled syntheses of carotenoid oxidative metabolites, (-)-loliolide, (-)-xanthoxin, and their stereoisomers
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We achieved the stereocontrolled syntheses of (-)-loliolide, (-)-xanthoxin, and their stereoisomers from (+)- or (-)-3-alkoxy-6-hydroxymethyl-1,1,5-trimethylcyclohexene through the corresponding syn and anti-epoxides, respectively, which were obtained by utilizing the highly diastereoselective Sharpless asymmetric epoxidation or mCPBA oxidation.
- Kuba, Masako,Furuichi, Noriyuki,Katsumura, Shigeo
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p. 1248 - 1249
(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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- Syntheese du (+/-)-loliolide ou hydroxy-6 teetrahydro-5,6,7,7a trimeethyl-4,4,7a(4H) benzofurannone-2 (6S,7aR) par cyclisation de l'acide homogeeranique
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Starting from pure homogeranic acid 2, in a stereoselective fashion, we describe a new synthesis of (+/-)-loliolide 1.Cyclization of 2 with mercury trifluoroacetate or phenylselenyl chloride provides the isohydroactinidiolide 6 which was converted to the
- Zamarlik, Henri,Gnonlonfoun, Noukpo,Rouessac, Francis
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p. 2326 - 2329
(2007/10/02)
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- SYNTHESE DU (+/-) LOLIOLIDE PAR POLYCYCLISATION DE L'ACIDE HOMOGERANIQUE.
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A new synthesis of (+/-) loliolide was achieved from pure homogeranic acid in a stereospecific fashion.The intermediate ethylenic lactone 6 was converted to the racemate of lol
- Rouessac, Francis,Zamarlik, Henri,Gnonlonfoun, Noupko
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p. 2247 - 2250
(2007/10/02)
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