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- W2953290119 abstract "Abstract The stereoselective synthesis of dl -siccanin (1) and dl -siccano-chromene E (2) has been described. Acid isomerization of nonconjugated octalone 11a, derived from known octalone 5, stereoselectively provided cis-fused octalone 12, from which cis -drimane aldehyde 31 was obtained. After condensation of 31 with lithio-orcinol dimethyl ether, the product 32 was treated with pyridinium chloride to give tetrahydrofuran 33 whose complete stereostructure was unambiguously established by an X-ray crystal analysis. While cyclization of monophenol 34, obtained by partial demethylation of 33, with sulfuric acid afforded siccanochromene E methyl ether (35), reaction of 34 with Lewis acid gave siccanin methyl ether (36) along with 35. In the latter cyclization, the formation of 36 was demonstrated to occur from initially formed 35. Finally, demethylation of 35 and 36 provided 2 and 1, respectively. A novel tetrahydrofuran formation by a neighboring participation, which was observed in hydroxy ketone 24 and diol 32, are also discussed." @default.
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- W2953290119 date "1987-07-07" @default.
- W2953290119 modified "2023-09-27" @default.
- W2953290119 title "ChemInform Abstract: Total Synthesis of dl-Siccanin and dl-Siccanochromene E." @default.
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- W2953290119 doi "https://doi.org/10.1002/chin.198727314" @default.
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