ja4008722_si_001.pdf (10.2 MB)
Total Synthesis of 6‑Deoxyerythronolide B via C–C Bond-Forming Transfer Hydrogenation
journal contributionposted on 2016-02-19, 16:50 authored by Xin Gao, Sang Kook Woo, Michael J. Krische
The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date.