Synthesis of Dibenzo‐Fused 15‐Membered Dioxa‐ketone Macrocycles through Ring‐Closing Metathesis Reaction

Abstract

We have developed a simple method for cross‐aldol condensation reaction to provide (1E,4E)‐1‐(2‐(allyloxy)aryl)‐5‐(2‐(allyloxy)aryl)penta‐1,4‐dien‐3‐ones (7 a–j) and (E)‐1‐(2‐(allyloxy)aryl)‐5‐(2‐(allyloxy)aryl)pent‐1‐en‐3‐ones (8 a–e) in 67–88 % and 73–86 % yields, respectively. Subsequently a series of dibenzo‐fused 15‐membered dioxa‐ketone macrocycles 9 a–j (61‐95 %) and 10 a–e (70‐90 %) have been synthesized from 7 a–j and 8 a–e, respectively, through ring‐closing metathesis reaction employing Grubbs’ third generation catalyst. The cis/trans‐configurations of products (9 a–j) and (10 a–e) were established from their 1H‐NMR spectral data.

Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones

“…NMR spectra of 2,6-DA-4-THTP S-oxides. References [62][63][64][65][66][67][68][69][70][71][72][73] are cited in Supplementary Materials file.…”

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

“…The naturally occurring compounds possessing macrocyclic skeletons have exhibited remarkable biological activities including antibiotic, anticancer, immunosuppressant, Hsp90 inhibitor, cytotoxic, etc. 1 Nonactin and valinomycin, a class of oxygen-bearing macrocycles, are examples of naturally occurring antibiotics obtained from Streptomyces species. 2 The actinoallolides, a family of complex polyketides, show potent activity against Trypanosoma protozoan parasites causing Chagas disease and African trypanosomiasis.…”

“…After garnering information about such research articles, we have realized in our limited knowledge that a recent review on the topic synthesis of bioactive macrocyclic compounds involving RCM strategy has still not been targeted upon. As we are currently engaging in the synthesis of macrocyclic compounds and subsequently we have published an article, 1 we decided to write a review article mentioning the synthetic routes developed since 2000, to graft bioactive macrocycles using RCM methodology. We are hopeful that this review will benefit researchers who are working in the field of medicinal chemistry to facilitate the development of novel macrocyclic compounds required for drug discovery.…”

Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition

“…anticancer, antibacterial, antifungal, immunosuppressant and more, and thus have proven themselves to be extremely effective in the field of medicine. 3 In particular, 1,2,3-triazole-fused macrocycles have exhibited promising biological activities such as anticancer, 4 5 6 antibacterial, 7 anti-inflammatory, 8 antiviral, 9 and more; 10 11 12 hence, the synthesis of triazole-based macrocycles has become a hot topic for researchers. Published reports revealed that significant efforts have been made towards the synthesis of triazole scaffolds involving Ag(I)-, Cu(I)-, and Ru(II)-catalyzed azide–alkyne cycloaddition (AAC) reactions, microwave-assisted reactions, and ultrasound-promoted reactions etc.…”

“…Through a literature survey, we realized that no recent review on the synthesis of bioactive 1,2,3-triazole fused macrocycles was available. Being currently engaged in the synthesis of macrocycles, 14 we herein report a review article summarizing the synthetic protocols undertaken to construct bioactive triazole-fused macrocycles since 2006. Throughout the article, we focus on CuAAC and RuAAC reactions that have been utilized for the preparation of 1,2,3-triazoles.…”