A short and efficient synthesis of (±)-trans-sabinene hydrate

Galopin, Christophe

doi:10.1016/s0040-4039(01)01081-4

Cited by 45 publications

(23 citation statements)

References 13 publications

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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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“…[48] Galopin entwickelte eine kurze und çkonomische Synthese des Naturstoffs, vermutlich um für den Einsatz von trans-Sabinen-Hydrat als Lebensmittelzusatzstoff zu werben. [49] Die Behandlung von Isovaleraldehyd (62)…”

Section: Synthese Von Roseophilinunclassified

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

et al. 2012

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Katalytische Umwandlungen mit N‐heterocyclischen Carbenen (NHCs) haben sich als effiziente Ansätze zum Aufbau komplexer Moleküle erwiesen. Seit der Veröffentlichung von Stetter 1975 zur Totalsynthese von cis‐Jasmon und Dihydrojasmon durch Carbenkatalyse hat sich die Anwendung von NHCs in der Totalsynthese, insbesondere in den letzten zehn Jahren, schnell verbreitet. Dieser Aufschwung ist zweifellos die Folge neuerer Entwicklungen bei NHC‐katalysierten Reaktionen, einschließlich der neuen Benzoin‐, Stetter‐, Homoenolat‐ und Aroylierungsprozesse. Die Umwandlungen ermöglichen ebenso typische wie auf Umpolung beruhende Bindungsbildungen und sind bereits als Schlüsselschritte in mehreren neuen Totalsynthesen aufgetreten. Dieser Kurzaufsatz beschreibt diese neuen Arbeiten und zeigt die verstärkten Einsatzmöglichkeiten der Carbenkatalyse in der Totalsynthese auf.

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“…[48] Galopin designed a short and economical synthesis of the natural product, presumably to promote the use of trans-sabinene hydrate as a food additive. [49] Treatment of isovaleraldehyde (62) generated dicarbonyl compound 64 in 82 % yield (Scheme 11). A base-promoted aldol cyclization yielded cyclopentenone 65.…”

Section: Synthesis Of (Ae)-trans-sabinene Hydratementioning

confidence: 99%

A Continuum of Progress: Applications of N‐Hetereocyclic Carbene Catalysis in Total Synthesis

et al. 2012

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N-Heterocyclic carbene (NHC) catalyzed transformations have emerged as powerful tactics for the construction of complex molecules. Since Stetter’s report in 1975 of the total synthesis of cis-jasmon and dihydrojasmon by using carbene catalysis, the use of NHCs in total synthesis has grown rapidly, particularly over the last decade. This renaissance is undoubtedly due to the recent developments in NHC-catalyzed reactions, including new benzoin, Stetter, homoenolate, and aroylation processes. These transformations employ typical as well as Umpolung types of bond disconnections and have served as the key step in several new total syntheses. This Minireview highlights these reports and captures the excitement and emerging synthetic utility of carbene catalysis in total synthesis.

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A short and efficient synthesis of (±)-trans-sabinene hydrate

Cited by 45 publications

References 13 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

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

A Continuum of Progress: Applications of N‐Hetereocyclic Carbene Catalysis in Total Synthesis

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