著者

平間 正博

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.41, no.5, pp.418-431, 1983

被引用文献数

3

---

Convergent and enantiospecific syntheses of compactin (1 a) and mevinolin (1 b), potent competitive inhibitor of HMG-CoA reductase, have been achieved via asymmetric intramolecular Diels-Alder reaction of acyclic (<I>E, E, E</I>) -trienone 4 leading to <I>trans</I>-octalone 3, a common intermediate for congeners. Chirality of C13 in 4 was designed to induce the four asymmetric centers with desired configuration by this reaction : the chirality controlled the approach of the dienophile from a single diastereotopic face. Trienone 4 was expeditiously constructed by the combination of two segments 5 and 6. Enantio- and stereo-specific synthesis of 6, a chiral 1, 3, 5- triol derivative, rested on the two novel methodologies, <I>i.e</I>, the convenient asymmetric reduction of β-keto carboxylate 19 d with baker's yeast and the regio- and stereo-selective iodofunctionalization (1, 3-asymmetric induction) of homoallylic carbamate. Preparation of 5 in its optically active form was accomplished by the elaboration of readily available γ-lactone 12.