Total Synthesis of (±)-Furanether A

Abstract

The first total synthesis of (±)-furanether A, which exhibits good antifeedant activity, has been concisely achieved in 13 linear steps. Notably, the key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]­octane moiety with two vicinal quaternary carbon centers was rapidly constructed in one step through a unique tandem C–H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization sequence.

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

“…The Tsuji-Wilkinson decarbonylation of aldehyde 15 was successfully conducted, leading to the formation of (−)-16 with a yield of 63% and 99% ee as determined by HPLC. 35,36 Removing the N-Ts group from (−)-16 gave a free amine that underwent Pictet-Spengler ring closure with formic acid 22,37,38 to produce the bridged pentacyclic product 17 in 71% yield over two steps.…”

A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

“… [133] Differently bridged oxa and aza skeleton could be prepared from one starting material which is the advantage of this protocol. In addition this scheme also prepared the analog of furanether B natural product [132] …”

“…Tetracyclic furansesquiterpenes, furanether A [132] and furanether B both have the core 1‐methyl‐8‐oxabicyclo[3.2.1]octane. Furanether A acts as an inhibitor in the antifeedant activity test.…”

Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro-4H-furo[3,4-c]pyran Derivatives through Pd-Catalyzed Formal (3 + 3) Allylic Cycloaddition of 2-Butene-1,4-diols with 2-(1-Alkynyl)-2-alken-1-ones

“…3,4-Fused furans exist extensively in bioactive natural products and important pharmaceuticals (Figure ). They have also been employed as versatile building blocks for the synthesis of complex heterocycles and key intermediates for the synthesis of natural products . Many methods have been developed for the synthesis of 3,4-fused furans, i.e., intramolecular intercepted Meyer–Schuster (M–S) rearrangement of cyclic 6-hydroxyhex-2-en-4-ynals, transfer oxygenative [2 + 2 + 1] cycloaddition of silyldiynes with nitrones, conia-ene reaction/radical cyclization sequence of ε- or ξ-ketoalkynes, desymmetric cycloisomerization of diynes, ring expansion of alkynones, domino reaction of propargylamines with β-keto esters, [2 + 2 + 1] annulation of 1,7-diynes with H 2 O, and cycloisomerization of diynes with pyridine N -oxide .…”