Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts

Iwaya, Kazuki; Tamura, Mutsuko; Nakamura, Momoe; Hasegawa, Eietsu

doi:10.1016/j.tetlet.2003.10.083

Cited by 23 publications

(10 citation statements)

References 14 publications

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“…Cha and co-workers reported that bromoalkynes (149) can be used for the β-functionalization of cyclopropyl alcohols (148) under Cu catalysis (Scheme 36). 90 These conditions are amenable to a number of substrates.…”

Section: β-Functionalization With C(sp 2 )−X and C(sp)−x Electrophilesmentioning

confidence: 99%

“…Soon after, Hasegawa and co-workers showed that benzotropolones could be synthesized by the oxidative ring opening of 263 (Scheme 62). 148 Ceric ammonium nitrate (CAN) was found to be effective in the oxidative ring opening, as other oxidants typically seen with oxidative ring opening of cyclopropyl alcohols such as FeCl 3 proved to be ineffective. Both the free cyclopropyl alcohol 263 as well as the TMSprotected derivative were effective in this chemistry, and yields using the protected analogue were generally found to be higher (Scheme 62).…”

Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

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Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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The carbon–carbon (C–C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C–C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C–C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor–acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.

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Section: β-Functionalization With C(sp 2 )−X and C(sp)−x Electrophilesmentioning

confidence: 99%

Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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“…It is still being used but entails limited variability of the substitution pattern. Multistep routes to 3,4-benzotropolone comprise the functionalization of benzocycloheptenones and ring expansions . A route to ether-annulated 3,4-benzotropolones by an intramolecular 1,3-dipolar cycloaddition was extended to making polycyclic 3,4-benzotropolones by hetero-Diels–Alder reactions …”

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confidence: 99%

Syntheses of 3,4-Benzotropolones by Ring-Closing Metatheses

Arican

Brückner

2013

Org. Lett.

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“…Also, we applied these methods to the oxidative ring-opening reaction of bicyclic keto cyclopropanol 11, and the expected benzotropolone 12 was obtained although not optimized (Scheme 4). 21 When 11 was subjected to method A using BTF as the solvent, incomplete reaction occurred giving a low yield of 12 (29% based on 53% conversion of 11) after treatment with NaOAc. On the other hand, method B in CH 2 Cl 2 completely consumed 11 and produced 12 in moderate yield (37%).…”

Section: Resultsmentioning

confidence: 99%