Synthesis of 11-aminodrim-7-ene from drimenol

Kuchkova, K. I.; Arycu, A. N.; Vlad, P. F.

doi:10.1007/s10600-009-9341-y

Cited by 16 publications

(8 citation statements)

References 20 publications

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“…Due to this potential, drimenol have been used as a base material to obtain other more active natural drimanes or semi-synthetic derivatives with an increased biological activity (KUCHKOVA et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

Drimys brasiliensis essential oil as a source of drimenol

Zem

Zuffellato-Ribas

Koehler

et al. 2016

HOLOS

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Drimys brasiliensis Miers is a native plant species to the Atlantic Forest, commonly known as cataia, and used as a stimulant, anti-diahrreal, antipyretic, among other properties. Dried and fresh leaves of cataia were collected in autumn/2012, submitted to hydrodistillation in a Clevenger graduated apparatus over a period of 4 hours after reaching the boiling point, then essential oil was collected. In oil from green leaves, 49 compounds were identified, being 65.0% sesquiterpenes, 12.0% monoterpenes and 23.0% other substances. In oil from dry leaves, 40 compounds were identified, being 76.1% sesquiterpenes, 2.0% monoterpenes and 21.9% other compounds. The main constituents in green leaves were germacrene D (8.9%), bicyclegermacrene (5.3%), epialpha-cadinol (5.1%), alpha-cadinol (6.0%), and drimenol (9.3%). In dry leaves the main constituents were germacrene D (6.3%), (E)-nerodidol (5.4%), spathulenol (9.5%), epi-alpha-cadinol (5.5%), alpha-cadinol (6.7%), and drimenol (11.6%). Due to its composition, the species may possibly present some biological activities like antifungical, antibacterial, insectifuge, molluscicide, and also the pharmacological properties that the species may present.

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Section: Resultsmentioning

confidence: 99%

Drimys brasiliensis essential oil as a source of drimenol

Zem

Zuffellato-Ribas

Koehler

et al. 2016

HOLOS

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“…Sodium cyanamide reacted with 64 to give 11-guanidinodrimene (65) ( Figure 24). Vlad et al [37] prepared 11-aminodrim-7-ene (64) from drimenol in four steps, in an attempt to improve the previous reported synthesis [36], although (-)-drimenol in this case was synthesized as described before [14]. Synthetic (-)-drimenol was transformed in drimenal oxime 63, exactly by the same procedure reported before [36].…”

Section: Drimenol As Natural Chiral Synthon For Other Drimane Terpenomentioning

confidence: 99%

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Cortés

Delgado

Saitz

et al. 2011

Natural Product Communications

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Several reviews have been published on sesquiterpenes, and on drimane-type sesquiterpenes, going through drimenol and related compounds among others. However, to our knowledge, this is the first review exclusively on drimenol. Although, the main focus is on drimenol as a synthon for other drimane-type compounds, synthetic routes to obtain racemic and (-)-drimenol are summarized, as well as its isolation and determination of its configuration, in the early fifties. The reviewed synthetic routes start from natural (-)-drimenol as chiral synthon in most of cases, nevertheless total syntheses are considered as well. The strategies where racemic drimenol is involved begin with biomimetic cyclization of trans-farnesol. Microbiological procedures to functionalize the A ring of drimenol are also commented. The revision is classified according to the chemical structure of the final product, which mainly correspond to structures of natural occurrence, although other related derivatives are also analyzed.

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“…Urones et al [2] prepared dihydroxyamine 1 and its derivatives, Barrero et al [3] -hydroxylamine 2 and products of amino and/or hydroxy group derivatization ( Figure 1). Later, 11-aminodrim-7-ene 3 was synthesized from drimenol 4 [4][5][6]. Recently, 12-amino-11-dihomodrim-8-ol 5 and products 6 and 7 of its dehydration have been synthesized from sclareolide 8 [7] and 13-amino-14,15-dinorlabd-8(9)-ene 9 from sclareol 10 [8] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Nitrogen-Containing Drimane and Homodrimane Sesquiterpenoids from Sclareolide

Lungu¹

2015

ChemJMold

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Abstract. The synthesis of new nitrogen-containing drimane and homodrimane sesquiterpenoids in cycle B is reported. A comparative study of the microwave (MW) assisted synthesis of drimenone versus classical conditions has been done. The drimanic and homodrimanic oximes were prepared on the base of ketones derived from commercially available sclareolide. The drimanic amine was obtained by reduction of corresponding oxime with LiAlH 4 . The structure of novel compounds was confi rmed using IR, 1 H and 13 C NMR analyses.

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Synthesis of 11-aminodrim-7-ene from drimenol

Cited by 16 publications

References 20 publications

Drimys brasiliensis essential oil as a source of drimenol

Drimys brasiliensis essential oil as a source of drimenol

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Synthesis of New Nitrogen-Containing Drimane and Homodrimane Sesquiterpenoids from Sclareolide

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