Iridoids are a large family of natural monoterpenoid products, which are found in a number of folk medicinal plants used as bitter tonics, sedatives, hypotensives, remedies for wounds and skin disorders. Recently, this wide range of bioactivities encouraged us to investigate synthesis of a variety of iridoids, which are structurally characterized by a cis-fused cyclopenta[c]pyran ring system. We have accomplished the first and asymmetric total synthesis of a new iridoid lactone, 6-hydroxy-7-(hydroxymethyl)-4-methylenehexahydrocyclopenta[c]pyran-1-(3H)-one. The key features of our synthesis includes stereoselective Pd(0)-catalyzed allylic alkylation and silicon-tethered radical cyclization of the cyclopentenol intermediate via Stork-Nishyama procedure, which provided contiguous four stereogenic centers of the target iridoid lactone.

Enantioselective total synthesis of natural iridoid lactone

243rd National Meeting (2012)

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