P-52 ブレビオン類の合成研究(ポスター発表の部)

概要

論文の詳細を見る
Breviones A-E were isolated from an active broths of Penicillium brevicompactum by Macias. These compounds were discovered to inhibit the growth against etiolated wheat coleoptiles. Because of the intriguing structural features, e.g., pentacyclic diterpene/polyketide hybrid structures including the spiro D ring and the cross conjugated cycloheptadienone moiety for breviones C and D, an interesting biological profile and limited availability, breviones represent attractive targets for total synthesis. We report here the first and enantioselective total syntheses of (+)-brevione A, (+)-brevione B and (+)-brevione C employing a convergent strategy. The synthetic route developed here features; i) the diastereoselective oxidative coupling of the 1,3-diene moiety and α-pyrone leading to the formation of the five membered spiro ring, ii) the [7-endo] mode of acyl radical cyclization for the elaboration of the cycloheptanone moiety of the A-ring.
天然有機化合物討論会の論文
2005-09-15