Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
Program in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
J Org Chem. 2022 Jan 7;87(1):386-398. doi: 10.1021/acs.joc.1c02417. Epub 2021 Dec 14.
Palodesangrens A and C along with the common tetracyclic core are prepared from simple benzaldehyde and acetophenone derivatives in a 10-step longest linear sequence which featured the Diels-Alder reaction forming the cyclohexene moiety, LiAlH isomerization, stereoselective acid-catalyzed cyclization forming the chroman moiety, regioselective iodination/vinyl Suzuki cross-coupling reaction, and ring-closing metathesis (RCM) forming the 2-pyran-2-one. Overall, the desired palodesangrens A and C are obtained in 6.1% and 6.4% yields, respectively.
从简单的苯甲醛和苯乙酮衍生物出发，通过 10 步最长线性序列制备 Palodesangrens A 和 C 以及常见的四环核心，该序列的特征在于 Diels-Alder 反应形成环己烯部分、LiAlH 异构化、立体选择性酸催化环化形成色满部分、区域选择性碘化/乙烯基铃木交叉偶联反应和闭环复分解（RCM）形成 2-吡喃-2-酮。总的来说，分别以 6.1%和 6.4%的产率得到目标 Palodesangrens A 和 C。
