Schinortriterpenoide: eine Fallstudie in Synthesedesign

The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

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Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

Bhat

Rashid

Sengupta

et al. 2020

Asian J Org Chem

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Total Synthesis of an Atropisomer of the Schisandra Triterpenoid Schiglautone A

Zhao

et al. 2018

Angewandte Chemie

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Adiastereoselective approach for the total synthesis of an unusual atropisomer of the Schisandratriterpenoid (AE)schiglautone Ai sd escribed. The efficient synthetic strategy features three key transformations:1)two sequential titanium-(III)-catalyzed radical cyclization/homologation reactions to construct the trans-fused [6,7] bicycle as well as install the quaternary carbons at C10 and C14 with the desired stereochemistry;2 )a Claisen rearrangement followed by ar ingclosing metathesis to forge the strained nine-membered ring; and 3) as ubstrate-controlled Michael addition to enable the introduction of the C17 side-chain with good diastereoselectivity.

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Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B

et al. 2019

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Ahighly convergent strategy for the synthesis of the natural product (À)-rubriflordilactone B, and the proposed structure of (À)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with ac ommon AB ring aldehyde precedes rhodium-catalyzed [2+ +2+ +2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone Ba nd provides arobust platform for further synthetic and biological investigations.

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Schinortriterpenoide: eine Fallstudie in Synthesedesign

Cited by 8 publications

References 92 publications

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

Total Synthesis of an Atropisomer of the Schisandra Triterpenoid Schiglautone A

Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B

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