The development of polyquinane chemistry

Paquette, Leo A.

doi:10.1007/bfb0048476

Cited by 143 publications

(25 citation statements)

References 360 publications

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“…Sesquiterpenes that have a tricyclo[6.3.0.0 1,5 ]undecane core (also called angular triquinanes), which is indeed a [5.5.5]fenestrane scaffold, are isolated particularly often ( Figure 12). [29] They can be grouped into four subcategories, depending on the positions of the substituents: isocomanes, [30,31] silphinanes, [32] silphiperfolanes, [33] and pentalenanes. [34] A member of the diterpenoid family, aflavinine (5), which was isolated from Aspergillus flavus, has a [6.6.6]fenestrane scaffold ( Figure 13).…”

Section: Methodsmentioning

confidence: 99%

Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

et al. 2013

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The scaffold of fenestranes is quite unique, as it contains four condensed cycles and a distorted tetracoordinated central carbon atom with bond angles greater than the regular 109°28". In this Minireview, a detailed overview on the developments regarding this compound class, including their synthesis, is given for the time period since 2006. In the past years, natural products that belong to the class of heterofenestranes have been isolated and their syntheses will also be discussed.

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Section: Methodsmentioning

confidence: 99%

Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

et al. 2013

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“…Hydroxy-2-methoxycarbonyl-6~-methyl-cis-bicyclo~3.3.O~oct-2-ene (2) To a soln of Hg(OAc)2 (1.69 g; 5.337 mmol) in water (10 ml) and THF (10 ml) at O°C was added (950 mg; 5.337 mmol). After stirring at 0 ' for 1 h successively a 15 % NaOH soln (6 ml) and a 15 % NaOH soln with 0.5 M NaBH4 (6 ml) was added.…”

Section: -Methoxycarbonyl-cis-bicyclo~330~oct-2-ene-6-onementioning

confidence: 99%

“…The approaches based on the intermediacy of bicyclol3.3.0loctenes hiqhly depend on general methods for constructing these precursors with a correct functional array. Recent approaches involving diquinanes as iridoid intermediates have been reported by Whitesell', Isoe', Fleming", Demuth and Schaffner", by Wender12 and by iridoids functionalized at C-11 (such as loganin (L), 8-epiloganin (2) and mussaenoside (1)) must therefore logically be directed towards intermediates of type A. However correct timing of the double bond formation is of the uttermost importance in connection with the possible presence of a double bond (& : F = double bond) in ring A during functional group interconversion in that ring.…”

mentioning

confidence: 98%

Iridoids: The Total Synthesis of the Aglucones of (±)‐8‐Epiloganin and (±)‐Mussaenoside Via Bicyclo |3.3.0| Octenes

Storme¹,

Callant²,

Vandewalle³

1983

Bulletin des Soc Chimique

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fused bicyclol3.3.0[octanes or diquinanes as potential intermediates for C-11 functionalized iridoids. The isoxazolidine 7 was obtained in four steps from the commercially available 2-cyclopentene-l-;?cetic acid 4. nalized diquinanes 0 to 19 and 11 to 2 have been prepared. examples of iridoid-syntGsis, compounds 21 and 26, the 0-methyl protected aglucones of (t) -8-epiloganin (2) and (?)ZussaeGside (1) have been synthesized starting from the common key-intermediate g.

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“…Chemistry of triquinane natural products has been an area of extensive synthetic studies since the mid-1970s [1][2][3][4]. Subergorgic acid is an angular sesquiterpene triquinane with a silphiperfolane skeleton (1) [5,6].…”

Section: Introductionmentioning

confidence: 99%