Recent Applications of Birch Reduction in Total Synthesis of Natural Products

Abstract

The Birch reduction is unique, in synthetic approaches, due to the adaptable substitution patterns of the substituted cyclohexa-1,4-and 1,3-dienes, particularly enol ethers. Birch reduction as a key and sometimes as the only reduction tool has found several applications in total synthesis of several natural occurring compounds. This name reduction is very important and quite useful for reduction of aromatic and none-aromatic moieties. It is particularly useful in aromatic compounds due to its selectivity of reduction of certain double bonds, which are present in one of the starting materials in multi-step total synthesis. It is also applicable when further reduction of nonaromatic moieties as a part of natural product structures, is required. In this report, we try to highlight the applications of this reaction as a key step in the total synthesis of natural products. It covers the applications of Birch reduction in total synthesis of naturally occurring compounds from 2003 till date.

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

“…We also are kin to update the applications of name reactions in the total synthesis of natural products [118][119][120][121][122][123][124][125][126][127][128] and applications of different synthons, reagents and catalysts in organic synthesis [129][130][131][132][133][134][135] .…”

Synthesis of 1,4‐Cyclohexadiene Carboxylates through a Formal [2+4]‐Cycloaddition of Propiolates under Cobalt Catalysis

“…Another synthetic strategy to target this skipped diene-motif inside a ring is to use the corresponding aromatic compounds and submit them to dissolved metal (Birch) reduction conditions (Scheme 1,B). [14,15] Unfortunately, this strategy does not yield the desired selectivity as the carboxylate directs the reduction to the ipso position. Recently, Hall and co-workers published a new method for the [2 + 4] cycloaddition of propiolic acid with 1,3-dienes using boron catalysis under very mild conditions.…”

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

“…In recent years, our research group showed interest and focused on the applications of name reactions in the total synthesis of natural products . Among them, in 2012 we published a report, covering the applications of SMCR in the total synthesis of natural products in Tetrahedron, which has seemingly attracted much attention of synthetic organic chemists due to numerous citations it has gained till date.…”