An improved synthesis of the [5.6.7]-tricyclic core of cyrneine B and glaucopine C. Issue 19 (7th September 2020)

• Record Type: Journal Article
• Authors: Wu, Guo-Jie; Han, Xiu
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 19(2020)
• Page Start: 2960
• Page End: 2964
• Publication Date: 2020-09-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo00758g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A strategically new route for an efficient synthesis of [5.6.7]-tricyclic 9, which could serve as an advanced intermediate, was presented. Abstract : A new route for the synthesis of the [5.6.7]-tricyclic core structure of cyrneine B and glaucopine C is presented. The key transformations included an efficient Suzuki cross-coupling of the densely substituted cyclopentenyl triflate with cyclic vinylboronate and a highly regio- and stereoselective intramolecular deconjugative alkylation. The synthetic route allowed for the construction of the [5.6.7]-tricyclic core within a 16-step linear sequence from the commercially available 2-methylcyclopentanone, which is five steps shorter than the first generation route as reported previously by us.