The synthesis of drimane sesquiterpenoids

Jansen, B. J. M.; Groot, Aede de

doi:10.1039/np9910800319

Cited by 74 publications

(28 citation statements)

References 58 publications

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“…The fractions eluted with light petroleum-EtOAc (4 : 1) yielded isotadeonal 14,15 (3, 1.67 g, 3.13% on dry plant material) and elution with light petroleum-EtOAc (3 : 1) successively gave polygodial 9,13 (2,4.35 g, 8.15%) and isodrimeninol 16 (4, 400 mg, 0.75%). Finally, the fractions eluted with light petroleum-EtOAc (1 : 1) provided drimendiol 10,12 (1, 504 mg, 0.94%). The isolated sesquiterpenoids showed physical (m.p., [˛] D ) and spectroscopic (IR, MS) data identical with those reported previously for these compounds.…”

Section: Extraction and Isolationmentioning

confidence: 99%

A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

Rodrı́guez

Zapata

Medina

et al. 2004

Magnetic Reson in Chemistry

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Section: Extraction and Isolationmentioning

confidence: 99%

A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

Rodrı́guez

Zapata

Medina

et al. 2004

Magnetic Reson in Chemistry

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“…Several syntheses of them have been developed because most of them are difficultly accessible compounds and occur in trace quantities as complicated mixtures in natural sources [2][3][4]. However, many of the syntheses are multi-step and inefficient.…”

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confidence: 99%

Enantioselective synthesis of 11-homodrim-7-en-9α,12,13-triol

et al. 2011

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The enantioselective synthesis of 11-homodrim-7-en-9D,12,13-triol, a convenient synthon for preparing polyfunctional 11-homodrimane sesquiterpenoids, was carried out starting from norambreinolide, a cleavage product available from several bicyclic labdane diterpenoids.One of the main motivators for the unwavering interest of chemists in drimane sesquiterpenoids is their broad spectrum of biological activity [1,2]. Several syntheses of them have been developed because most of them are difficultly accessible compounds and occur in trace quantities as complicated mixtures in natural sources [2][3][4]. However, many of the syntheses are multi-step and inefficient. In addition, the starting compounds are not always readily available.In contrast with drimane sesquiterpenoids, homodrimane (tetranorlabdane) compounds are more available because they can be prepared by relatively simpler methods from readily available labdane diterpenoids (sclareol, larixol, abienols, manool, manoyloxides, and zamoranic, communic, and labdanolic acids, etc.) [5].The preparation of tetranorlabdane derivatives has been often reported. Several of these derivatives have been widely applied in the perfume, cosmetic, and tobacco industries owing to their amber aroma. Judging from the literature, most homodrimanes have not been tested for types of activity other than organoleptic. However, it was recently found that 11-homopolygodial (1) had antifeedant activity greater than that of natural polygodial (2) [6]. Therefore, it seemed interesting to synthesize polyfunctional homodrimanes.Herein results from the synthesis of 11-homodrim-7-en-9D,12,13-triol (3) from commercially available norambreinolide (4) are reported.Norambreinolide (4) was reduced by LiAlH 4 by the literature method [7] to sclarodiol (5), which was identified by comparison with an authentic sample. Diol 5 was acetylated under standard conditions by a mixture of acetic anhydride and pyridine. According to TLC, the reaction products included the desired 12-monoacetate of sclarodiol (6) and an impurity of a less polar compound that was separated by chromatography over a column of SiO 2 (Scheme 1). Hydroxyacetate 6 was identified by comparison with an authentic sample that was obtained by us earlier [8]. Its spectral properties agreed with those published [9-10]. Reaction of 6 with triphenylphosphine and iodine by the literature method [11] formed a mixture of unsaturated acetates 7, in which the isomer with the tetra-substituted double bond dominated (64%) according to NMR spectroscopy. The contents of the isomers with the tri-substituted and exocyclic double bonds were 19 and 17%, respectively. Dehydration of 6 by phosphoryl chloride in pyridine afforded a product in which the isomer with the exocyclic double bond dominated [12]. The mixture of acetates 7 was oxidized by sodium chromate by the literature method [13] to 12-acetoxy-11-homodrim-8-en-7-one (8) (60% yield).Ketoacetate 8 was reacted with N-bromosuccinimide (NBS) in order to functionalize the C-13 methyl. This produced 12...

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“…The great variety and strength of the biological activities 1 of these compounds have greatly stimulated the development of general synthetic routes for them. 2 Following the authors' research on the synthesis of bioactive drimanes from (-)-sclareol (1) 3,4 and (-)-drimenol (6), [5][6][7][8] active compounds 2 and 4 have been prepared. 11,12-Epoxydrim-8,12-en-11-ol (2) was isolated by Capon et al from a marine sponge of the genus Dysidea, 9 but these authors were unable to fully characterize this drimane due to its considerable instability.…”

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Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

Cortés

et al. 1999

J. Nat. Prod.

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The synthesis of drimane sesquiterpenoids

Cited by 74 publications

References 58 publications

A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

Enantioselective synthesis of 11-homodrim-7-en-9α,12,13-triol

Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

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The synthesis of drimane sesquiterpenoids

Cited by 74 publications

References 58 publications

A complete 1H and 13C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

A complete 1H and 13C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

Enantioselective synthesis of 11-homodrim-7-en-9α,12,13-triol

Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

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A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii

A complete ¹H and ¹³C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii