- A Total Synthesis of 8β-Hydroxycycloaraneosene by Means of an Eight-Membered Ring-Formation via a Lewis Acid-Catalyzed Ene Reaction. Confirmation of Its Natural Occurrence
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An improved eight-membered ring closure by means of a Lewis-acid-catalyzed ene reaction was applied to the synthesis of cycloaraneosene and its congener, "hydroxycycloaraneosene".Comparisons of the NMR spectral data of the synthetic and natural compounds established that the natural product possesses an 8β-hydroxy structure, not the originally proposed 9α-hydroxy one.
- Kato, Nobuo,Wu, Xue,Tanaka, Shinya,Takeshita, Hitoshi
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- Structure Elucidation of "Hydroxycycloaraneosene" by Unambiguous Total synthesis. An Eight-Membered Ring Formation via a Lewis Acid-Catalyzed Ene-Reaction
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An improved eight-membered ring closure by means of a Lewis acid-catalyzed ene-reaction of an iridoid dimer produced a tricyclic derivative wich was further converted to cycloaraneosene and its congener, "hydroxycycloaraneosene".Total synthesis of the latter established its structure to be 8β-hydroxy derivative, not as the originally-proposed 9α-.
- Kato, Nobuo,Wu, Xue,Tanaka, Shinya,Takeshita, Hitoshi
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- Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of "epi"-Fusicoccane Diterpenoids, and the Structure Revision of Its Congener, Hydroxycycloaraneosene
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The 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via the stereoselective condensation of two units of optically active iridoids, Cope rearrangement and chemical reduction of the tetrasubstituted C=C bond.The NMR spectrum of synthetic 9α-hydroxycycloaraneosene was not identical with the congener product, and the natural alcohol is likely to be 8β-hydroxyl derivative.
- Kato, Nobuo,Tanaka, Shinya,Takeshita, Hitoshi
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- Synthetic Photochemistry. XLII. Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of 5-8-5-Membered Tricyclic Diterpenoid from Sordaria araneosa
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A 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via a stereoselective condensation of two units of optically active iridoids, a Cope rearrangement, a chemical reduction of the tetrasubstituted double bond, and the formation of an eight-membered ring.The proposed structure of natural hydroxycycloaraneosene should be revised to 8β-hydroxycycloaraneosene, judging from the NMR spectral data.
- Kato, Nobuo,Tanaka, Shinya,Takeshita, Hitoshi
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p. 3231 - 3238
(2007/10/02)
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