Polysubstituted naphthalenes from phthalide ortho esters and dienophiles

Contreras, L.; Slemon, Clarke E.; MacLean, David B.

doi:10.1016/s0040-4039(01)95190-1

Cited by 15 publications

(3 citation statements)

References 10 publications

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“…The viability of using a Diels−Alder cycloaddition reaction to append an anthraquinone to each of the synthetic quinone imines described above was investigated initially in the 15,18-dideoxydynemicin series, using 1,1-diethoxyphthalan as a precursor to the unstable Diels−Alder diene 1-ethoxyisobenzofuran . Because the quinone imines 78 and 79 were more readily accessible than the dynemicin A precursor 6 , they were investigated first in model studies.…”

Section: Synthesis Of (+)-Dynemicin a (1)mentioning

confidence: 99%

“…The viability of using a Diels-Alder cycloaddition reaction to append an anthraquinone to each of the synthetic quinone imines described above was investigated initially in the 15,18dideoxydynemicin series, using 1,1-diethoxyphthalan as a precursor to the unstable Diels-Alder diene 1-ethoxyisobenzofuran. 45 Because the quinone imines 78 and 79 were more readily accessible than the dynemicin A precursor 6, they were investigated first in model studies. Heating a solution of the quinone imine 78 with excess 1,1-diethoxyphthalan (22 equiv) and glacial acetic acid (1.6 equiv) in toluene at reflux for 20 min afforded a 1:1 mixture of endo and exo Diels-Alder adducts 80 and 81, respectively, in 60% yield.…”

Section: Synthesis Of (+)-Dynemicin a (1)mentioning

confidence: 99%

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A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability

et al. 1997

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In a similar fashion, bis(triphenylphosphine)palladium(II) chloride (3.64 g, 5.17 mmol, 0.050 equiv) was added (at 0 oC) and the resulting mixture was deoxygenated once again at-78 oC. The deoxygenated reaction suspension was then warmed to 23 oC and was stirred at that temperature for 3 h. The brown product solution was washed with a 1:1 mixture of saturated aqueous potassium carbonate solution and saturated aqueous ammonium chloride solution (3 x 150 mL). The organic layer was dried over sodium sulfate and was concentrated. The residue was purified by distillation under reduced pressure (bp 45-50 oC, 0.5 mm Hg) to afford (Z)-1-chloro-4-(tertbutyldimethylsilyl)-1-buten-3-yne (32) as a colorless oil (12.5 g, 60%

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Section: Synthesis Of (+)-Dynemicin a (1)mentioning

confidence: 99%

Section: Synthesis Of (+)-Dynemicin a (1)mentioning

confidence: 99%

A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability

et al. 1997

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“…' Overall versatility is again limited in 3 5 4 5 these procedures either by nature of the precursor ' or by conditions of isobenzofuran generation ' which preclude the isolation of non-aromatised products.…”

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A new method for the generation of isobenzofurans: A simple entry to substituted naphthalenes

Keay

Lee

Rodrigo

1980

Tetrahedron Letters

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Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

Koning¹,

Georgiou²,

Michael³

et al. 2021

Organic Reactions

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This chapter provides a detailed survey of the Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura annulation reactions, as reported in the literature through March 2021. These reactions provide an efficient means for the synthesis of polycyclic aromatic compounds and related systems. The mechanism, scope, and limitations of each annulation reaction are covered, and typical methods for the preparation of the requisite starting materials (phthalides, homophthalic anhydrides, and related precursors) are provided. Applications of these annulation reactions as key steps in the synthesis of selected aromatic natural products are included, as are representative experimental procedures for accomplishing the annulation reactions.

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Polysubstituted naphthalenes from phthalide ortho esters and dienophiles

Cited by 15 publications

References 10 publications

A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability

A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability

A new method for the generation of isobenzofurans: A simple entry to substituted naphthalenes

Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

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