Abstract A convenient and highly efficient synthesis of optically pure trans-(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.

This study presents a convenient, large-scale synthesis of optically pure trans-(+)-sobrerol using 8 steps and 26% overall yield, with key intermediate 4 prepared in high yield using lipase as catalyst.

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A Convenient, Large Scale Synthesis of trans-(+)-Sobrerol

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