著者

砂塚 敏明 長光 亨 大村 智

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.56, no.6, pp.478-488, 1998-06-01

参考文献数

37

被引用文献数

2

---

The first total synthesis of the microbial a-pyrone meroterpenoid, (+) -pyripyropene A (1), acyl-CoA : cholesterol acyltransferase (ACAT) inhibitor, which is effective and concise convergent approach (14 steps, 9.3% overall yield), designed to afford easy access to both the natural products and a variety of analogs, has been achieved. The key step is the coupling reaction between a-pyronepyridine moiety (4) and the acid chloride of sesquiterpene moiety (3) in the presence of Lewis acid to construct ketone (2). The sesquiterpene moiety has been synthesized started from (+) -Wieland-Miescher ketons via stereoselective reductive formylation, palladium associated carbonylation, and allylic oxidation.<BR>(+) -Pyripyropene E (36) also has been synthesized from farnesyl acetate (9 steps, 9.6% overall yield). The convergent and stereoselective route exploited a biomimetic polyene cyclization as the key transformation.