Synthesis of a dimeric pyranonaphthoquinone via a novel double furofuran annulation strategy

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

“…[96] Earlier, monomeric pyranonaphthoquinones such as kalafungin, [97] nanaomycin A, frenolicin B [98] and arizonin C1 [99] had been synthesized by them by use of the furofuran annulation strategy. [96] Earlier, monomeric pyranonaphthoquinones such as kalafungin, [97] nanaomycin A, frenolicin B [98] and arizonin C1 [99] had been synthesized by them by use of the furofuran annulation strategy.…”

“…In 1998 Brimble and co-workers artfully synthesized the dimeric pyranonaphthoquinones 82 and 83, the structures of which are closely related to that of 5, for the first time (Scheme 5). [96] Earlier, monomeric pyranonaphthoquinones such as kalafungin, [97] nanaomycin A, frenolicin B [98] and arizonin C1 [99] had been synthesized by them by use of the furofuran annulation strategy. They extended this strategy to the synthesis of dimer molecules.…”

“…Because these strategies did not yield 77 in higher yields, Brimble and co-workers continued with the earlier approach based on Suzuki-Miyaura coupling to get 77 (Scheme 5). [96] In continuation of their work on dimeric molecules, in 2003 Brimble and co-workers classically extended the furofuran annulation strategy to crisamicin A (2, Scheme 7). [104] Considering the biaryl linkage in 2 to be different from that in 5 they attempted the synthesis of regioisomeric bisacetyl compound 100 (regioisomer to 86, Scheme 6).…”

Recent Applications of the Suzuki—Miyaura Cross‐Coupling Reaction in Organic Synthesis

“…297 Johnson such as 340a and 340b have been prepared by using the SM cross-coupling protocol of the bromonaphthalene 338 with the pinacolborane 339 as the key steps (Scheme 149). 302 Walsh et al approach towards the synthesis of non-adride-related compounds such as 348. Here, the SM cross-coupling and intramolecular cyclisation of dimeric bis-anhydride compounds were used as the key steps (Scheme 152).…”

Synthesis of Dityrosine Cross-Linked Peptide Dimers Using the Miyaura−Suzuki Reaction

“…Biaryls are common byproducts in the palladium-catalyzed Miyaura reaction of aryl halides with bispinacolatodiboron, and a palladium-catalyzed Ullmann homocoupling with bispinacolatodiboron has been used in the synthesis of dimeric pyranonaphthoquinones . We hypothesized that the Miyaura−Suzuki reaction might be efficiently applied to the formation of intermolecular dityrosine cross-links as opposed to intramolecular macrocyclic ring closure reactions.…”