Total synthesis of dl-trans-sabinene hydrate, and related monterpenes

Fanta, Wayne I.; Erman, William F.

doi:10.1021/jo01268a081

Cited by 41 publications

(22 citation statements)

References 2 publications

(3 reference statements)

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“…The optimum conditions for elution of components 1 and 2 and separation from polar trans-thujan-4-ol were 2% diethyl ether in pentane, which suggested an only slightly polar character of the compounds. Analysis of the 1 H-NMR spectra of the two components revealed their similarity to the spectra of well-known and previously described thujan-4-ols (sabinene hydrates), [9][10][11][12] which suggested that we might be dealing with thujan-4ol analogues. The main feature differentiating the spectra of unknown compounds and thujan-4-ol was a singlet with integration equivalent to three hydrogen atoms, the chemical shift of which was 3.25 p.p.m.…”

Section: Resultssupporting

confidence: 58%

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Composition of essential oil from seeds of Nigella sativa L. cultivated in Poland

Wajs

Bonikowski

Kalemba

2008

Flavour & Fragrance J

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Forty-eight compounds have been identi¼ed in the essential oil from Nigella sativa (black cumin) seeds, 14 of which are volatiles that have never been isolated from black cumin before. This is the ¼rst time to show two monoterpenoids: cis-and trans-4-methoxythujane, occur naturally in plants, speci¼cally in the essential oil from N. sativa seeds in 0.3% and 4%, respectively. The structures of the 4-methoxythujanes were established by both spectroscopic and chemical methods.SEED ESSENTIAL OIL OF NIGELLA SATIVA L. 127 tr, trace (<0.05%); RI exp , experimental retention index given for CP-Sil5 column; RI lit , literature retention index given for CP-Sil5 column. 18 * New compounds for essential oil of N. sativa. 130 A. WAJS ET AL. 5 32.1 (d) 1 . 1 8 ( dd, 1H, J = 3.8/8.5 Hz) 32.8 (d ) 1 . 0 0 ( dd, 1H, J = 3.8/7.9 Hz) 34.4 (d) 1 . 0 6 ( dd, 1H, J = 3.5/8.2 Hz) 33.6 (d) 1 . 0 4 ( dd, 1H, J = 3.7/7.9 Hz) 6 12.1 (t) 0 . 1 5 ( dd, 1H endo , J = 3.8 Hz J gem = 4.9 Hz) 11.7 (t) 0 . 3 3 ( dd, 1H exo , J gem = 5.0 Hz, J = 7.9 Hz) 13.2 (t) 0 . 2 2 ( dd, 1H endo , J = 3.5 Hz, J gem = 5.1 Hz) 11.1 (t) 0 . 3 2 ( dd, 1H exo , J gem = 5.0 Hz, J = 7.9 Hz) 0.38 (dd, 1H exo , J gem = 4.9 Hz, J = 8.5 Hz) 0.64 (dd, 1H endo , J = 3.8 Hz, J gem = 5.0 Hz) 0.40 (dd, 1H exo , J gem = 5.1 Hz, J = 8.2 Hz) 0.64 (dd, 1H endo , J = 3.7 Hz, J gem = 5.0 Hz) 7 30.8 (d) 1 . 5 2 ( sp, 1H, J = 6.8 Hz) 29.9 (d ) Scheme 1. Synthesis of cis-and trans-4-methoxythujanes from sabinene and from appropriate thujan-4-ols

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Section: Resultssupporting

confidence: 58%

“…The cis-trans con¼guration was con¼rmed by comparison between the NMR spectra recorded for both compounds with the corresponding ones described in the literature. [9][10][11][12][13] Conversion of the alcohols to methyl ethers was accomplished in the reaction with dimethyl sulphate (Scheme 1).…”

mentioning

confidence: 99%

Composition of essential oil from seeds of Nigella sativa L. cultivated in Poland

Wajs

Bonikowski

Kalemba

2008

Flavour & Fragrance J

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“…Finally, IR spectrum of peak 8 was found to be identical with that of authentic (+ )-trans-sabinene hydrate (3) 11,12). …”

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confidence: 77%

“…According to the method reported by Fanta et al, 11) cis-and tralls-sabinene hydrate were synthesized and separated into the cis-form (80 mg, mp 29°C) and trans-form (20 mg, mp 60~ 62°C) by preparative gas chromatography.…”

Section: Analytical and Preparative Gas Chromatographymentioning

confidence: 99%

Mentha candicans, a New Chemical Strain of SectionSpicatae, Containing trans-Sabinene Hydrate as the Principal Component of Essential Oil

Karasawa

Shimizu

1978

Agricultural and Biological Chemistry

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The essential oil of Mentha candicans Miller, obtained by solvent extraction, was found to contain predominantly (+ )-trans-sabinene hydrate, accompanied by a small amount of (+ )-cis-sabinene hydrate; the latter compound was for the first time isolated as a naturally occurring monoterpene. When the oil was obtained by the usual steam distillation, transsabinene hydrate was isomerized to terpinen-4-ol, the content of which increased markedly with prolonged distillation. The other components of this oil were a-pinene, tJ-pinene, sabinene, 1,8-cineole, r -terpin ene, p-cymene, 3-octanol, menthol and a-terpineol. These findings indicate that Mentha candicans is a new chemical strain of Section Spicatae.

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“…pating solvents have not been studied extensively, and essential details concerning the course of events are unknown. Ozonolysis of 1,3-cyclohexadiene gave a mixture of oxalic acid and succinic acid (1); ozonolysis of 1-methyl-4-isopropyl-1,3-cyclohexadiene in methanol, followed by reduction with sodium iodide in acetic acid, gave 2-methyl-3,6-dioxoheptane (2). Ozonolysis of naphthalene ( l a ) and of the substituted naphthalenes lb-d in methanol afforded in each case the hemiperacetal 2a, and Id gave, additionally, the peracetal 2d (3).…”

Section: Introductionmentioning

confidence: 99%

Ozonolyses of 1,4-disubstituted 1,3-cyclohexadienes and of related compounds in methanol

Griesbaum¹,

Mertens²,

Jung³

1990

Can. J. Chem.

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Ozonolyses of 1,4-dimethyl-( 5 a ) and of 1-methyl-4-isopropyl-1,3-cyclohexadiene ( 5 6 ) in methanol occur stepwise by sequential cleavage of the two double bonds. Monoozonolysis products are the corresponding compounds 6 and 7, and diozonolysis products are the corresponding cyclic peroxides 19,20, and 21. By contrast, ozonolysis of the non-conjugated diene 2,5-dimethyl-l,5-hexadiene (13) in methanol occurs by simultaneous mono-and diozonolysis to give 14, 16a, 18a, and 20a.Key words: ozonolysis, 1,3-cyclohexadienes, 3-hydroperoxy-l,2-dioxanes, 2,5-bis-hydroperoxy-2,5-dimethoxyhexane, 3-hydroxy-l,2-dioxanes, 3,6-dimethoxy-l,2-dioxanes. 1369 (1990). L'ozonolyse, dans le mkthanol, des 1,4-dimCthyl-(5a) et 1-mCthyl-4-isopropyl-cyclohexa-1,3-dikne ( 5 6 ) se produit par des clivages par Ctape des deux doubles liaisons. Les produits de monoozonolyse sont les composCs 6 et 7 alors que les produits de diozonolyse sont les peroxydes cycliques correspondants 19,20 et 21. Par opposition, l'ozonolyse dans le mCthanol d'un dikne non-conjuguC, comme le 2,5-dimkthyl-hexa-l,5-dikne (13), provoque des mono-et des di-ozonolyses simultanCes qui fournissent les produits 14, 16a, 18a et 20a.Mots elks : ozonolyse, cyclohexa-1,3-diknes, 3-hydroperoxy-1,2-dioxanes, 2,5-bis-hydroperoxy-23-dimCthoxyhexane, 3-hydroxy-l,2-dioxanes, 3,6-dimkthoxy-l,2-dioxanes.[Traduit par la revue]Introduction the cyclodienes 5a and 5b, and of the acyclic substrates 13 and Ozonolysis reactions of conjugated cyclic diolefins in particiin at ca. -750C. pating solvents have not been studied extensively, and essential details concerning the course of events are unknown. Ozonolysis of 1,3-cyclohexadiene gave a mixture of oxalic acid and succinic acid (1); ozonolysis of 1-methyl-4-isopropyl-1,3-cyclohexadiene in methanol, followed by reduction with sodium iodide in acetic acid, gave 2-methyl-3,6-dioxoheptane (2). Ozonolysis of naphthalene ( l a ) and of the substituted naphthalenes lb-d in methanol afforded in each case the hemiperacetal 2a, and Id gave, additionally, the peracetal 2d (3). Compounds 3 and 4 have been postulated, yet not proven, as intermediates for 2a and 2d, respectively. Similar results were reported for the ozonolysis of 1-methylnaphthalene (4) and of substituted 2-methoxynaphthalenes (5) in methanol.

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Total synthesis of dl-trans-sabinene hydrate, and related monterpenes

Cited by 41 publications

References 2 publications

Composition of essential oil from seeds of Nigella sativa L. cultivated in Poland

Composition of essential oil from seeds of Nigella sativa L. cultivated in Poland

Mentha candicans, a New Chemical Strain of SectionSpicatae, Containing trans-Sabinene Hydrate as the Principal Component of Essential Oil

Ozonolyses of 1,4-disubstituted 1,3-cyclohexadienes and of related compounds in methanol

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