Structure Determination and Mechanism of Formation of a <i>seco</i>-Moreliane Derivative Supported by Computational Analysis

Chacón-Morales, Pablo A.; Amaro-Luis, Juan M.; Kutateladze, Andrei G.

doi:10.1021/acs.jnatprod.7b00041

Cited by 6 publications

(1 citation statement)

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“…An interesting molecular rearrangement has been reported by Morales and co-workers [5]. They observed that triketone 5 on treatment with p-TSA in benzene resulted in the formation of a keto lactone 6, a 1-11 seco-moreliane derivative and also the first representative of this group (Figure 1).…”

Section: Acid Catalyzed Rearrangement Of Moreliane Based Triketone Csupporting

confidence: 53%

Recent Developments in Selected Sesquiterpenes: Molecular Rearrangements, Biosynthesis, and Structural Relationship among Congeners

Paknikar¹,

Fondekar²

2018

Terpenes and Terpenoids

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Recent developments in selected sesquiterpenoids are reviewed for the past one decade (2005-2017) with special reference to Mechanisms of multistep molecular rearrangements of some sesquiterpenes or derivatives based on isotopic labeling studies and extensive spectroscopic analysis such as molecular rearrangement of acetyl cedrene to cedrene follower, acid catalyzed rearrangement of moreliane-based triketone, synthesis of (−)-isocomene and (−)-triquinane by acid-catalyzed rearrangement of (−)-modhephene, Total synthesis of (+)-cymbodiacetal, BF 3 catalyzed molecular rearrangements of mono epoxides of α-and β-himachalenes, santonic acid: Zn-HCl-ether reduction. Insights into biosynthesis of albaflavenone, caryol-1(11)-ene-10-ol, (+)-koraiol, pogostol, patchouli alcohol and valerenadiene are discussed. Congeners for probing structure-biosynthetic relationship. This approach is discussed with the availability of very interesting results on the isolation of highly oxygenated secondary metabolites from endophytic fungi, Xylaria sp.

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Section: Acid Catalyzed Rearrangement Of Moreliane Based Triketone Csupporting

confidence: 53%