Total Synthesis of (±)‐Dihydroisosubamol. Issue 5 (23rd December 2016)

• Record Type: Journal Article
• Authors: Pflästerer, Daniel; Rudolph, Matthias; Yates, Brian F.; Ariafard, Alireza; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 5(2017)
• Page Start: 866
• Page End: 874
• Publication Date: 2016-12-23
• Subjects: Dibenzocycloheptanoides -- natural products -- total synthesis -- dibenzocycloheptenes -- gold; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600663
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: We herein report the first total synthesis of the dibenzocycloheptanoide (±)‐dihydroisosubamol. The key step includes a recently developed gold‐catalysed hydroarylation reaction for the construction of the dibenzocycloheptene motif. Additional steps are a Suzuki‐Miyaura cross coupling, a palladium‐catalysed hydroxylation and an allylic oxidation. To access the saturated seven‐membered ring system an iridium‐catalysed hydrogenation proved to be successful. Abstract :