A New Method for the Synthesis of Stipitatic Acid Isomers: Photooxygenation of Ethyl 6H-Cyclohepta[d][1,3]dioxole-6-carboxylate

Daştan, Arif; Saraçoğlu, Nurullah; Balcı, Metin

doi:10.1002/1099-0690(200109)2001:18<3519::aid-ejoc3519>3.0.co;2-2

Cited by 28 publications

(22 citation statements)

References 15 publications

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“…43 In this elegant work, cyclohexatrienes generated through cyclopropanation/6π electrocyclic ring-opening on 1,3-benzodioxole were oxidized with singlet oxygen to generate endoperoxides. Subsequent treatment with cobalt tetraphenylporphorine promoted the rearrangment to αHTs.…”

Section: Synthetic Access To α-Hydroxytropolonesmentioning

confidence: 99%

The biology and synthesis of α-hydroxytropolones

et al. 2014

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α-Hydroxytropolones are a subclass of the troponoid family of natural products that are of high interest due to their broad biological activity and potential as treatment options for several diseases. Despite this promise, there have been scarce synthetic chemistry-driven optimization studies on the molecules. The following review highlights key developments in the biological studies conducted on α-hydroxytropolones to date, including the few synthetic chemistry-driven optimization studies. In addition, we provide an overview of the methods currently available to access these molecules. This review is intended to serve as a resource for those interested in biological activity of α-hydroxytropolones, and inspire the development of new synthetic methods and strategies that could aid in this pursuit.

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Section: Synthetic Access To α-Hydroxytropolonesmentioning

confidence: 99%

The biology and synthesis of α-hydroxytropolones

et al. 2014

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“…114 This was applied to the synthesis of stipitatic acid isomers as discussed in later sections. 115 Tropolones could also be prepared with appropriate alkoxy substituents on the cycloheptatriene substrate. 116–117 …”

Section: Conversion Of Simple Seven-membered Ring To Tropones and mentioning

confidence: 99%

“…115 A base-mediated Kornblum-DeLaMare rearrangement 113 and cobalt meso -tetraphenylporphyrin-catalyzed (CoTPP) rearrangement of this endoperoxide led to isomers of stipitatic acid esters 36-4A/B .…”

Section: Synthesis Of Naturally Occurring Tropones and Tropolonesmentioning

confidence: 99%

Synthesis of naturally occurring tropones and tropolones

et al. 2014

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Tropones and tropolones are an important class of seven-membered non-benzenoid aromatic compounds. They can be prepared directly by oxidation of seven-membered rings. They can also be derived from cyclization or cycloaddition of appropriate precursors followed by elimination or rearrangement. This review discusses the types of naturally occurring tropones and tropolones and outlines important methods developed for the synthesis of tropone and tropolone natural products.

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“…A similar regiodiversity was earlier observed for a 1 O 2 peroxygenation of 3,4-dihydroazulen-1(2H )-one 408,409 . Treatment of symmetric 1,3-dioxolane-fused cycloheptatriene 532 with singlet oxygen affords the single cyclic peroxide 533 in very high yield (Scheme 148) 410 . Reaction of 1 O 2 with 7-methoxy-1,3,5-cycloheptatriene (534a) gives the bridged bicyclic peroxide 536a in good yield through [4 + 2]-cycloaddition to the parent tropilidene form (Scheme 149) 411,412 .…”

Section: Cycloaddition Of Singlet Oxygen With 13-dienesmentioning

confidence: 99%