88243-64-5

Upstream product

• 20482-11-5 (+)-davanone 
• 1448011-56-0 ethyl (2S)-2-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propanoate 
• 1448011-58-2 dimethyl {(3S)-3-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]-2-oxobutyl}phosphonate 
• 1150633-83-2 (2S)-N-methoxy-N-methyl-2-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propanamide 

Relevant academic research and scientific papers

Synthesis of cis- and trans -davanoids: Artemone, hydroxydavanone, isodavanone, and nordavanone

A concise and versatile synthesis of both cis and trans diastereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of trans-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between cis and trans products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time. Georg Thieme Verlag Stuttgart New York.

TETRAHYDROFURAN-TYPE TERPENOIDS FROM TANACETUM VULGARE

Investigation of a rare genotype of Tanacetum vulgare afforded a series of tetrahydrofuran-type terpenoids, whose pattern was different in flowers and leaves.The major constituent of the flowers was the trans Δ3,4-hydroperoxide of davanone, whereas the leaves gave mostly a peroxyhemiketalic compound resulting from the intramolecular cyclization of the cis Δ3,4-hydroperoxide of davanone.Structures were elucidated by spectral data and chemical reactions, including correlation with natural (+)-davanone.The peroxyhemiketalic compound upon acylation of its hydroxyl group gave an instantaneous complex reaction, resulting in the formation of a β-acyloxyenone and loss of one molecule of acetone.Among the minor constituents of the leaves, a C-10 carboxylic acid biogenetically related with davanone was isolated.Key Word Index - Tanacetum vulgare; Compositae; sesquiterpenes; davanone; hydroperoxides; peroxyhemiketals; chemotaxonomy.

AN UNUSUAL NEROLIDOL DERIVATIVE FROM ARTEMISIA INCULTA

The aerial parts of Artemisia inculta afforded a new nerolidol derivative named arteincultone, - Key Word Index - Artemisia inculta; Compositae; sesquiterpene; nerolidol derivative; artemetin.