576. Taxine. Part II. Glycol cleavage fragments from O-cinnamoyltaxicin-I

Langley, Benjamin; Lythgoe, B.; Scales, B.; Scrowston, R. M.; Trippett, S.; Wray, Dennis

doi:10.1039/jr9620002972

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“…Requiring the optically active cyclohexenones 2 and 5 in both antipodal forms for the preparation and olfactive evaluation of precious flowery and woody natural [14] and synthetic [15] fragrances, we decided to employ the same methodology that we had previously developed for the preparation of campholenal analogues [ 161. The appropriately substituted cyclopentenes 1 (Scheme I ) ') For racemic material, see: 2c: [6], 3a: [7], 312: [XI, 5a: [9], 5b: [lo], 6a: 1111, 6b: [lo], 6c: [12]. Results and Discussion.…”

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Preparation of optically active cyclohexenones: Chirons for the lipophilic moiety of flowery‐ and woody‐like odorant ketones

Chapuis¹,

Brauchli²,

Thommen³

1993

Helvetica Chimica Acta

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Optically active 2,5,6,6-and 2,4,4,5-tetraalkylcyclohex-2-en-l-ones ((+)-Za4 and (-)-5a4), impoI;tant building blocks for flowery-and woody-like odorants, have been prepared. Compounds (+)-Za-d and (-)-5a4 were obtained by ozonolysis of the corresponding cyclopentenic precursors, followed by intramolecular aldol condensation. Alternatively, enones (+)-2a4 were reduced to the corresponding allylic alcohols and converted to enones (-)-Sad via acidic isomerization and oxidation. 13C-NMR assignments are presented.Introduction. -2,5,6,6-and 2,4,4,5-Tetraalkylcyclohex-2-en-l-ones are important and characteristic building blocks for the lipophilic part of many fragrances 11 J and carotenoids [2]. To our knowledge, despite the tremendous work on this subject [3], only

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confidence: 99%