Synthese des (R)‐trans‐11‐Hydroxy‐8‐dodecensäure‐lactons (Recieifeiolid)

Synthesis of Recifeiolide The synthesis of the mould metabolite recifeiolide (VIII), a 12‐membered ring lactone, is described. 1,3‐Butandiol was resolved with (−)‐camphanic acid via ( R )‐1‐iodo‐3‐butanol (II) into ( R )‐3‐hydroxybutyl triphenyl phosphonium iodide (III). Wittig condensation of the phosphorane derived from III with methyl 8‐oxo‐octanoate (V) led to the methyl trans ‐11‐hydroxy‐8‐dodecenoate (VI). The corresponding hydroxy acid VII was transformed into the S‐(2‐pyridyl) carbothioate which cyclizes under the influence of silver ion to the lactone VIII. With (−)‐( R )‐1,3‐butandiol (I) as starting material the naturally occurring (+)‐( R )‐recifeiolide (VIII) is produced in 70% yield from VII.