Double furofuran annulation to a bis-naphthoquinone: an approach to dimeric pyranonaphthoquinones

Brimble, Margaret A.; Duncalf, Letecia J.; Neville, Daniel

doi:10.1039/a805031g

Cited by 22 publications

(16 citation statements)

References 23 publications

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“…6, 7 The stereochemistry of hemiacetals 13a and 13b was assigned by analogy to the monomeric system 6,7 and a dimeric analogue of actinorhodin. 11 The 13 C NMR spectrum was also consistent with the proposed structure and exhibited one set of signals for the individual carbons of the two diastereomers 13a and 13b with the methylene carbon at δ 35.7 being assigned to C-9 and the two methine carbons at δ 81. With furonaphthofuran adducts 13a and 13b in hand, attention next turned to the oxidative rearrangement step.…”

Section: Resultssupporting

confidence: 68%

“…10 We have previously reported the use of a double furofuran annulation-oxidative rearrangement strategy to prepare a dimeric pyranonaphthoquinone 5 that is structurally related to the aphid pigment actinorhodin 4. 11 It was envisaged that previous methodology employed for the synthesis of the actinorhodin analogue 5 could be applied to the synthesis of crisamicin A 1. Our strategy for the synthesis of crisamicin A 1 (Scheme 1) hinged on the double oxidative rearrangement of furonaphthofuran 6 to furonaphthopyran 7 as the key step with bisfuronaphthofuran 6 being formed by double furofuran annulation of bis-naphthoquinone 9 with 2-trimethylsilyloxyfuran 8.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of regioisomeric analogues of crisamicin A

Brimble

Lai

2003

Org. Biomol. Chem.

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The synthesis of bis-furonaphthopyrans 12a and 12b, regioisomeric analogues of the dimeric pyranonaphthoquinone antibiotic crisamicin A 1 is described. The key intermediate 16 was prepared via a one-pot in situ Suzuki-Miyaura homocoupling of naphthyl triflate 23 using bis(pinacolato)diboron. Oxidation of binaphthyl 16 to bis-naphthoquinone 14 was then effected with silver(II) oxide and nitric acid. Efficient double furofuran annulation of bis-naphthoquinone 14 with 2-trimethylsilyloxyfuran 8 afforded bis-furonaphthofuran adducts 13a and 13b as an inseparable 1:1 mixture of diastereomers. Oxidative rearrangement of this mixture of bis-furonaphthofuran adducts 13a and 13b using silver(II) oxide and nitric acid afforded unstable bis-furonaphthopyrans 12a and 12b also as a 1:1 mixture of diastereomers. Addition of 2-trimethylsilyloxyfuran 8 to naphthoquinone 25 afforded adduct 26 that underwent oxidative rearrangement to furonaphthopyran 27, however attempts to effect Suzuki-Miyaura homocoupling of triflates 26 and 27 to their respective dimers 13 and 12, was unsuccessful.

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Section: Resultssupporting

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Synthesis of regioisomeric analogues of crisamicin A

Brimble

Lai

2003

Org. Biomol. Chem.

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“…An excess of freshly distilled cyclopentadiene was added under nitrogen -78 o C to a dichloromethane solution of bis-naphthoquinone (1) which was prepared as reported previously [3]. After 10 min., no starting material remained and the formation of several new products of similar polarity was evident upon TLC analysis.…”

Section: Resultsmentioning

confidence: 99%

Diels-Alder Cycloaddition of Cyclopentadiene to a Bis-naphthoquinone

Brimble

Duncalf

2000

Molecules

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“…[102] The first approach involved construction of the binaphthalene moiety 85 from benzyl ether 84 through a Suzuki coupling reaction. [102] The first approach involved construction of the binaphthalene moiety 85 from benzyl ether 84 through a Suzuki coupling reaction.…”

Section: Double Furofuran Annulation Strategymentioning

confidence: 99%

“…In the same year (1998), Brimble and co-workers also reported attempted alternative strategies for the synthesis of bisnaphthoquinone 77 (Scheme 6). [102] The first approach involved construction of the binaphthalene moiety 85 from benzyl ether 84 through a Suzuki coupling reaction. [100] Subsequent acetylation and double Fries rearrangement provided, after several attempts, 87 in lower yields (competing reactions gave deacetylated product, monoacetyl compound, and regioisomeric aryl methyl ketones).…”

Section: Double Furofuran Annulation Strategymentioning

confidence: 99%

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

2016

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The dimeric pyranonaphthoquinones, “bis versions” of the naphtho[2,3‐c]pyran‐5,10‐dione moiety, comprises a group of antibiotics that have been isolated from a variety of sources including plants, bacteria, fungi, and insects. This review discusses the known naturally occurring dimeric pyranonaphthoquinones, their isolation and bioactivity, and synthetic approaches towards them that have helped to confirm their structures, as well as to resolve structural uncertainties such as stereochemistry. The major focus has been on the synthetic approaches adopted to complete the challenging total synthesis of the natural isolates and analogues.

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Double furofuran annulation to a bis-naphthoquinone: an approach to dimeric pyranonaphthoquinones

Cited by 22 publications

References 23 publications

Synthesis of regioisomeric analogues of crisamicin A

Synthesis of regioisomeric analogues of crisamicin A

Diels-Alder Cycloaddition of Cyclopentadiene to a Bis-naphthoquinone

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

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