Synthese de diterpenes tetracycliques du type hibane

Manh, Duc Do Khac; Fétizon, M.; Flament, Jean‐Pierre

doi:10.1016/0040-4020(75)87048-7

Cited by 25 publications

(14 citation statements)

References 16 publications

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“…Manool ketone 4 was identified by comparing 1 H and 13 C NMR data with published data [20]. The optical rotation of our product (+27) was close to the optical rotation found by Do Khac Manh (+38) [22] and Bolster et al (+36) [20] confirming the same absolute stereochemistry.…”

supporting

confidence: 83%

Epimanool and a New 2,6-Dideoxy-hexopyran-3-ulose Derivative from Celmisia viscosa

Sansom

Larsen

Evans

et al. 2013

Natural Product Communications

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Epimanool is reported for the first time in high yield (up to 7% w/w) from the New Zealand endemic shrub Celmisia viscosa (Asteraceae), together with a new derivative, containing the first natural example of a 2,6-dideoxy-hexopyran-3-ulose. The absolute stereochemistry of epimanool was proven by conversion to manool ketone, which also showed the potential of this plant as a source of perfume starting material. Epimanool is present in the sticky exudate on the leaf surfaces of C. viscosa.

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supporting

confidence: 83%

Epimanool and a New 2,6-Dideoxy-hexopyran-3-ulose Derivative from Celmisia viscosa

Sansom

Larsen

Evans

et al. 2013

Natural Product Communications

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“…[20] (Scheme). As described earlier [21], a sequence of KMnO, oxidation and ozonolysis transformed man001 (+)-7 into diketone 8 (48% overall yield). When diketone 8 in the vapor phase was allowed to pass through a quartz tube at 550" (residence time ca.…”

Section: ' )mentioning

confidence: 61%

Preparation and Odor Evaluation of Both Enantiomers of 3,4,4aα,5,6,7,8,8aβ‐Octahydro‐5,5,8aβ‐trimethyl‐2(1H)‐naphthalenone and 1,2α,3,4,4aβ,5,6,7,8,8aβ‐Decahydro‐5,5,8aβ‐trimethyl‐2β‐naphthalenyl Acetate, Four Woody Odorants

Gautier

Vial

Morel

et al. 1987

Helvetica Chimica Acta

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The enantiomeric decahydro-2-iiaphthaleiiols (+)-S and (-)-S were prepared by enantloselective hydrolysis of the raceink chloroacetate ( i ) -2 catalyzed by porcine pancreatic lipase, and converted to the corresponding acetates (+)-1 and (-)-1 and ketones (+)-6 and (--)-6. The absolute configurations or the ketones, alcohols, and acetates were establishcd by chemical corrclation with natural manool ((+)-7) by making use of a refro-ene cleavage reaction of the known manool degradation product 8 to (-)-6. A distinct odour difference bctween the two enmtiomers of each pair (+)-l/(--)-l and (+)-6/(-)-6 has been round.

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“…Finally, a tetracyclic structure similar to 6 was reported when labdadienes were treated with O 3 or NaIO 4 /OsO 4 system [14]. It is reported that allylic alcohols like (-)-sclareol or lab-13-en-8β-ol-15-oic acid (α,β-unsaturated methyl esters) were selectively oxidized to the corresponding methyl ketones with the KMnO 4 /MgSO 4 in acetone system [24,25]. Under these conditions, when compounds 3, 4 or a mixture of both were treated with KMnO 4 /MgSO 4 in acetone at room temperature, compound 7 was obtained selectively in 63% yield.…”

Section: Resultsmentioning

confidence: 99%