“…Removal of the silyl ether with 20% HF and acetylation of the resulting primary alcohol proceeded smoothly and set the stage for selective deprotection of the isopropyl ethers with AlCl 32 3. These three steps proceeded in 77% yield overall and gave synthetic propolisbenzofuran B ( 1 ) that displayed identical spectral data to that reported for the natural product (IR, 1 H, 13 C, MS).…”
The first total synthesis of propolisbenzofuran B, a bioactive natural product isolated from honeybee propolis resin, is reported. The convergent synthesis makes use of a silicon-tether controlled oxidative ketone–ketone cross-coupling and a novel benzofuran-generating cascade reaction to deliver the core structure of the natural product from readily prepared precursors.
“…Removal of the silyl ether with 20% HF and acetylation of the resulting primary alcohol proceeded smoothly and set the stage for selective deprotection of the isopropyl ethers with AlCl 32 3. These three steps proceeded in 77% yield overall and gave synthetic propolisbenzofuran B ( 1 ) that displayed identical spectral data to that reported for the natural product (IR, 1 H, 13 C, MS).…”
The first total synthesis of propolisbenzofuran B, a bioactive natural product isolated from honeybee propolis resin, is reported. The convergent synthesis makes use of a silicon-tether controlled oxidative ketone–ketone cross-coupling and a novel benzofuran-generating cascade reaction to deliver the core structure of the natural product from readily prepared precursors.
“…The hydroxyl group of the OH in position 3 was protected as isopropyl ether, which can be cleaved by acids, 20 if it is desired. Other MeO groups were already introduced into the building blocks.…”
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.