Concise total synthesis of (±)-pileamartines A and B. Issue 24 (15th November 2022)

• Record Type: Journal Article
• Authors: Xu, Wei; Wang, Taimin; Zhou, Xin; Fang, Lijing; Zhang, Chen; Zhai, Hongbin; Cheng, Bin
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 24(2022)
• Page Start: 6968
• Page End: 6972
• Publication Date: 2022-11-15
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01400a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A concise total synthesis of (±)-pileamartines A and B, a pair of alkaloids sharing an unprecedented tetracyclic skeleton, was achieved in 9 and 8 linear steps, respectively. Abstract : A concise total synthesis of (±)-pileamartines A and B, a pair of alkaloids sharing an unprecedented tetracyclic skeleton, was achieved in 9 and 8 linear steps, respectively. The key steps include an NHC-catalyzed tandem aza-benzoin/Michael reaction to rapidly establish the polyhydroindenopyrrole core, a diastereoselective reductive allylation of pyrrolidone, and an RCM to construct the piperidine ring.