Photoinduced vinylcyclopropane-cyclopentene rearrangement: A methodology for chiral bicyclo[3.2.0]heptenes. Formai syntheses of (±)-grandisol and naturally occurring ()-Δ9(12)-Capnellene and its antipode

Sonawane, H. R.; Naik, V.G.; Bellur, Nanjundiah S.; Shah, Virendra G.; Purohit, P.C.; Kumar, M.Uday; Kulltarni, Dilip G.; Ahuja, Jaimala R.

doi:10.1016/s0040-4020(01)91019-1

Cited by 22 publications

(6 citation statements)

References 45 publications

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“…A formal asymmetric synthesis of natural (−)-capnellene 29 was reported in 1991, based on the photoinduced vinylcyclopropane−cyclopentene rearrangement of the bicyclic alcohol 358, obtained from the natural (+)-3-carene 357 (Scheme 13). 348,349 This rearrangement delivered a mixture of diastereoisomers 359 and 360 in 75% yield. Subsequent transformations of this mixture allowed elimination of the undesired alcohol 360, leading to 361 in 39.8% yield over four steps.…”

Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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“…[210] Weitere Naturstoffe, die durch photochemische Umlagerungen eines Cyclohexan-anellierten Cyclohexadienons hergestellt wurden, sind (AE )-b-Vetivon, [211] (À)-Cyclocolorenon [212] und (À)-Axisonitril 3. [213] In den Synthesen der Sesquiterpene (AE)-Oplopanon [214] sowie (AE )-a-Cadinol und (AE )-3-Oxo-aCadinol [215] [219] Durch photoinduzierte Vinylcyclopropan-Umlagerungen gelangen Totalsynthesen von (+)-a-und (+)-b-Cyperon ausgehend von (À)-Epimaalienon, [220] sowie von (AE )-Grandisol (73) [221] und (À)-D [221] Durch eine [3,3]-Verschiebung eines Bicyclo[3.2.2]nonadienons konnte (AE )-Sesquicaren hergestellt werden. [222] Ein Chinon diente als Chromophor für die photochemische Isomerisierung von (+)-Komarovichinon zu (+)-Komarovispiron, die der vorgeschlagenen Biosynthese folgt.…”

Section: Umlagerungen Von Kreuzkonjugierten Cyclohexadienonenunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

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“…A formal asymmetric synthesis of (−)-capnellene ( 180 ) was achieved in 1991, based on the photoinduced vinyl-cyclopropane−cyclopentene rearrangement of the bicyclic alcohol 193 , which was obtained from (+)-3-carene ( 192 ) ( Scheme 42 ) [ 91 , 92 ].…”

Section: Chemical Synthesismentioning

confidence: 99%

Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Qiu

Lan

et al. 2018

Molecules

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Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I–VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.

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Photoinduced vinylcyclopropane-cyclopentene rearrangement: A methodology for chiral bicyclo[3.2.0]heptenes. Formai syntheses of (±)-grandisol and naturally occurring ()-Δ9(12)-Capnellene and its antipode

Cited by 22 publications

References 45 publications

Tricyclic Sesquiterpenes from Marine Origin

Tricyclic Sesquiterpenes from Marine Origin

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

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