Methodology for the Construction of the Bicyclo[4.3.0]nonane Core

Abstract

Abstract:The bicyclo[4.3.0]nonane scaffold, commonly known as a hydrindane, is a common structural motif found in many terpenoid structures and one that remains a challenge for synthetic chemists to elaborate with appropriate regio-and stereo-selectivity. Over the course of the study of terpene natural products, the elaboration of the hydrindane structure has seen progress on the utilization of both old and newer methods to achieve the desired outcomes. This review seeks to serve as a general overview of these methods, and detail specific examples.

Unveiling therapeutic efficacy of extract and multi-targeting phytocompounds from Christella dentata (Forssk.) Brownsey & Jermy against multidrug-resistant Pseudomonas aeruginosa

“…45 Moreover, terpenoids also exhibits various biological functions, ranging from anti-tumor effects and cardiovascular impacts to anti-inflammatory properties. 46 Ethyl acetate is known for its effectiveness in extracting terpenoids, 47 our research goal extended beyond terpenoids isolation alone. Ethanol, a more polar solvent than ethyl acetate, allows for the extraction of a wider array of bioactive compounds, including polyphenols, 48 flavonoids 49 and other polar constituents in addition to terpenoids which are of significant interest in our investigation.…”

Organocatalyst-mediated asymmetric one-pot/two domino/three-component coupling reactions for the synthesis of trans-hydrindanes

“…Bicyclo[4.3.0]nonane skeletons are known as hydrindanes, 8 and there are several natural products possessing trans -hydrindane skeletons such as isopulo'upone, 9 tamariscol, 10 and haliclonadiamine 11 ( Fig. 1 ).…”

Chasing Polycyclic Natural Products: 5/6/5‐ or 5/6/6‐Carbotricyclic Scaffold Construction via Stereodivergent Diels‐Alder Reaction of Chiral Hydrindanes and Their Boron Complexes

“…This hydrindane is also part of other natural products such as amaminol A [19] or pulo'upone [20] and several synthetic routes have been developed. [21][22][23][24] These routes include, among others, the functionalization of Hajos-Parrish ketones, [25,26] the Rauhut-Currier [27] tandem metathesis of endo-norbornenes [28] and Diels-Alder reactions [29,30] as well as the Dieckmann condensation [31] and more recently, singlet oxidation of furans combined with organocatalytic double Michael reaction. [32] Especially organocatalysis proved to be a powerful tool for the enantioselective construction of hydrindanes.…”

“…Both natural product families share the trans‐cis ‐substituted 5/6/5‐membered carbotricyclic scaffold containing the trans ‐hydrindane (bicyclo[4.3.0]nonane) core unit. This hydrindane is also part of other natural products such as amaminol A [19] or pulo'upone [20] and several synthetic routes have been developed [21–24] . These routes include, among others, the functionalization of Hajos‐Parrish ketones, [25,26] the Rauhut‐Currier [27] tandem metathesis of endo ‐norbornenes [28] and Diels‐Alder reactions [29,30] as well as the Dieckmann condensation [31] and more recently, singlet oxidation of furans combined with organocatalytic double Michael reaction [32] .…”