有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
α-ピロン環を有するメロ-テルペノイド・ピリピロペン類の合成研究
砂塚 敏明長光 亨大村 智
著者情報
ジャーナル フリー

1998 年 56 巻 6 号 p. 478-488

詳細
抄録

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.
(+) -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.

著者関連情報
© 社団法人 有機合成化学協会
前の記事 次の記事
feedback
Top