A novel, versatile synthetic approach to linearly fused tricyclopentanoids via photo-thermal olefin metathesis

Mehta, Goverdhan; Srikrishna, A.; Reddy, A. Venugopal; Nair, Mangalam S.

doi:10.1016/0040-4020(81)80021-x

Cited by 149 publications

(66 citation statements)

References 65 publications

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“…rel-(1 R.2 R,6 S,8 S,9 S. 13 S ) -l l -(Diphenylmethyliden) -1,4-dirnethyltetracycl0[6.6.0.0~~~.0~~~'] tetradec-l-en-3.14-dion (4). Ein Gemisch von 1,Ol g (5 mmol) 3a [5] 41,9 (d); 37,9 (1); 36,O ( t , 2 C); 18,2 ( 9 ) ; 9,9 (9). MS: 408 (100, M"), 260 (63), 232 (42), 205 (25), 203 (25), 191 (27), 177 (99), 167 (49, 149 (87), 91 (64), 69 (55) rel-(I R. 2R.…”

Section: Experimenteller Teilmentioning

confidence: 99%

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Polycyclopentane Als Steroid‐Analoga

Trachsel

Keese

1988

Helvetica Chimica Acta

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Section: Experimenteller Teilmentioning

confidence: 99%

“…-Ausgangspunkt fur die Synthese der Verbindungen vom Typ 2 war das von Mehta et al beschriebene Triquinan 3a, b [5]. Durch schrittweise Anellierung sollten sich daraus die gesuchten steroid-analogen Verbindungen herstellen lassen3).…”

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Polycyclopentane Als Steroid‐Analoga

Trachsel

Keese

1988

Helvetica Chimica Acta

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“…5 4 ) [268]. Ausgehend vom Triquinan 236 [269] wurde nacheinander auf HFLVETICA C H I M I~A ACTA ~ Vol. 75 (1992) beiden Seiten des Molekuls in sterisch einheitlich verlaufenden Reaktionen") je ein zus2tzlicher Cyclopentan-Ring anelliert.…”

Section: )unclassified

60 Jahre Steroid‐Chemie in Helvetica Chimica Acta

Kalvoda

1992

Helvetica Chimica Acta

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“…cyclic as well as acvclic 1 -3-dienes have served. as a result of their photochemical rearrangements, as a rich source of novel polycyclic ring systems (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). Three representative examples are shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…Three representative examples are shown in Scheme 1. Because, among other things, the presence of an aromatic double bond at the 6,7 -position would be expected to affect the formation of photoproducts analogous to 3, 6, and 8, we decided to prepare and photolyze the 6,7-benzo analogue of ene-dione 1, namely cis-4a,9a,9,10-tetrahydro-l,4-anthracenedione, 12 (Table 1). This paper reports the synthesis of compound 12 and five of its methylated and benzannelated derivatives; the photochemistry of these systems will be reported in a separate publication.…”

Section: Introductionmentioning

confidence: 99%

Trapping of o-quinodimethane with p-quinones: synthesis of tetrahydro-1,4-anthracenediones

Askari¹,

Lee²,

Perkins³

et al. 1985

Can. J. Chem.

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. Can. J. Chem. 63, 3526 (1985). Previous work from our laboratory has been concerned with investigating the photochemical reactivity of the tetrahydro-1,4-napthalenedione system, both in solution and the solid state. The results obtained prompted us to extend our studies to the analogous tetrahydro-l,4-anthracenedione system. The most direct method of synthesis of the desired compounds is through Diels-Alder addition of o-quinodimethane to p-quinones. Because of the ease with which the adducts would be expected to undergo bis-enolization to the corresponding hydroquinones, their preparation requires mild, neutral conditions. After much experimentation, success was achieved using the Durst-Charlton sulfur dioxide extrusion method for generating o-quinodimethane from 3,6-dihydro-l,2-oxathiin-2-oxide. In situ trapping.using p-benzoquinone and other substituted p-quinones afforded the desired adducts in reasonable yields. In the case of duroquinone and 2,3-dimethyl-l,4-naphthalenedione, fluoride ion-catalyzed generation of o-quinodimethane from [o-[cu-(trimethylsilyl)methyl]benzyl]trimethylamrnoniurn bromide by the method of Ito also gave acceptable results; however, the bis-enolizable adducts were not stable under these eaction conditions. SYED ASKARI, SUSAN LEE, ROBERT R. PERKINS et JOHN R. SCHEFFER. Can. J. Chem. 63, 3526 (1985). Dans un travail anttrieur rtalist dans notre laboratoire, on a examine la rtactivitt photochimique du systeme titrahydronaphtalbnedione-1,4 tant en solution qu'a l'ttat solide. Les rtsultats obtenus nous ont incitt a Ctendre nos ttudes au systbrne analogue de la tttrahydroanthracenedione-1,4. La rntthode la plus directe de synthese des composts dtsirts implique une addition de Diels-Alder du o-quinodimtthane sur des p-quinones. Compte tenu du fait qu'il est A prCvoir que les adduits subiront facilement une bis-enolisation conduisant aux hydroquinones correspondantes, il est important d'utiliser des conditions

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A novel, versatile synthetic approach to linearly fused tricyclopentanoids via photo-thermal olefin metathesis

Cited by 149 publications

References 65 publications

Polycyclopentane Als Steroid‐Analoga

Polycyclopentane Als Steroid‐Analoga

60 Jahre Steroid‐Chemie in Helvetica Chimica Acta

Trapping of o-quinodimethane with p-quinones: synthesis of tetrahydro-1,4-anthracenediones

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