Abstract
| - The synthesis of lairdinol A, a component of the host-selective phytotoxin depsilairdin, was achieved in12 steps (18% overall yield) without the use of protecting groups starting with the Diels−Alder reactionof (R)-carvone with 3-trimethylsilyloxy-1,3-pentadiene. The key step established the trans ring fusion bypreferential epoxidation of a trans-fused enone in an equilibrating mixture of the cis-fused and trans-fused diastereomers (i.e., equivalent to a dynamic kinetic resolution of these isomers). The synthesisconfirms the absolute configurations of lairdinol A and its enantiomer, cyperusol C.
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