By employing a base-promoted middle-to-terminal double epoxide-opening cascades, the C2-symmetric (�)-glabrescol was synthesized in two steps from (10S,11R)-dihydroxy-10,11-dihydrosqualene or squalene with 50% or 10% overall yields, respectively. The five tetrahydrofuran rings in glabrescol were constructed in one operation. The high efficiency of these syntheses makes them as two possible biogenetic pathways of (�)-glabrescol. The biomimetic syntheses of two other triterpene polyethers enshuol and armatol C from the same intermediate as glabrescol by applying endo epoxide-opening cascades are currently under investigation. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/242nm/uploads/88807__figure1_.jpg' alt='' />

Two two-step enantioselective total syntheses of (-)-glabrescol and the studies toward the total syntheses of enshuol and armatol C

245th National Meeting (2013)

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