Ahamad Jarish, Khatua Rashmi Ranjan, Khan Faiz Ahmed
Department of Chemistry, Indian Institute of Technology Hyderabad Sangareddy 502284 Telangana India
RSC Adv. 2025 Jul 31;15(33):27254-27259. doi: 10.1039/d5ra04830c. eCollection 2025 Jul 25.
This study presents a refinement of a synthetic protocol for the diastereoselective intramolecular ene-type cyclization of -prenylated chalcones using ZnCl, leading to the corresponding tertiary alcohols sans the undesired alkene by-product. While InCl·4HO offers the best yield, ZnCl with slightly diminished yield provides a cheaper alternative. To assess diastereoselectivity, the prenyl group was replaced with a cinnamyl moiety, forming a third consecutive chiral center as a single diastereomer. Additionally, total synthesis of (±) involucrasin C, along with the synthesis of several structurally related novel analogues, is presented in this work.
本研究提出了一种合成方案的改进方法，该方案用于使用ZnCl₂对γ-异戊烯基查尔酮进行非对映选择性分子内烯型环化反应，从而生成相应的叔醇，且无不需要的烯烃副产物。虽然InCl₃·4H₂O的产率最高，但产率略有降低的ZnCl₂提供了一种更便宜的替代方案。为了评估非对映选择性，将异戊烯基替换为肉桂基部分，形成了作为单一非对映异构体的第三个连续手性中心。此外，本工作还展示了(±)involucrasin C的全合成以及几种结构相关的新型类似物的合成。
