Scutorientalin D, a neo-clerodane diterpenoid from Scutellaria orientalis subsp. pinnatifida

Malakov, Peter Y.; Papanov, Georgi Y.; Spassov, S. L.

doi:10.1016/s0031-9422(96)00476-1

Cited by 25 publications

(18 citation statements)

References 18 publications

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“…Scutellaria alpina (Bozov et al, 1993(Bozov et al, , 1994de la Torre et al, 1995), Scutellaria orientalis subsp. pinnatifida (Malakov et al, 1997), S. alpina subsp. javalambrensis (de la Muñoz et al, 1997), S. orientalis subsp.…”

Section: Resultsunclassified

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

et al. 2010

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Section: Resultsunclassified

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

et al. 2010

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“…While ZnCl 2 , EtAlCl 2 , BF 3 ·Et 2 O and Eu(fod) 3 did not give acceptable yields of [4+2] cycloadducts, a full equivalent of Et 2 AlCl produced a remarkable enhancement in the reaction of 6 with dimethyl maleate or diethyl fumarate (Scheme 4). In the presence of Et 2 AlCl the cycloadduct endo-21 was obtained as a single diastereomer in 92% yield after only 1.5 h at 0 °C.…”

Section: Lewis Acid-promoted [4+2] Cycloaddition Reactions Of Dienes mentioning

confidence: 99%

The Enantiomeric Scaffold Approach to Highly Functionalized 1-Oxadecalines: Enantio- and Regiocontrolled [4 + 2] Cycloadditions of 5-Alkenyl-η³-Pyranylmolybdenum Complexes

2007

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TpMo(CO) 2 (5-alkenyl-η-2,3,4-pyranyl) diene complexes function as excellent chiral scaffolds for the efficient regio-and enantiocontrolled synthesis of highly functionalized 1-oxadecaline derivatives through a novel transition metal-mediated Diels-Alder reaction. Very good to excellent yields and excellent levels of endo-selectivity are obtained and the reaction gives products with complete retention of enantiomeric purity when carried out with chiral, non-racemic scaffolds. A subtle structural modification on the diene (replacement of an H by a trans-CH 3 group) leads to a complete change of regiochemistry, which is discussed from a mechanistic point of view. The role of the η 3 -coordinated TpMo(CO) 2 moiety is also critical to the further functionalization of the [4+2] cycloadducts, as illustrated by the preparation of 20 variously functionalized 1-oxadecaline derivatives (>98% ee when carried out with high enantiopurity scaffolds).

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“…Phytochemical researches on S. orientalis s.l. are the subject of several studies and, consequently, neo-clerodane diterpenoids and two phenethyl alcohol glycosides were isolated [5][6][7]. In addition, an essential oil research about Scutellaria orientalis subsp.virens, from Iran, is given by Delnavazi et al (2014) [8].…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition of the Essential Oil of Scutellaria orientalis L. subsp. virens (Boiss. Kotschy) J. R. Edm. from Turkey

Içen¹,

Arabacı²,

Köstekci³

et al. 2016

HJBC

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B u çalışmada, Malatya, Türkiye'den toplanan Scutellaria orientalis L. subsp. virens (Boiss. & Kotschy) J. R. Edm (Lamiaceae) bitkisinin uçucu yağının kimyasal kompozisyonu belirlenmiştir. Uçucu yağ, bitkinin toprak üstü kısımlarından su distilasyonu ile elde edilmiş ve gaz kromatografisi-kütle spektrometresi ile analiz edilmiştir. Scutellaria orientalis subsp. virens bitkisinin uçucu yağının %89.29' ini oluşturan 33 bileşik tespit edilmiştir. β-Karyofillen (%22.08), γ-Kadinen (%19.92), Kamfen (%6.00) ve Kalaren (%5.94) uçucu yağın ana bileşenleri olarak belirlenmiştir. Analiz sonuçları mevcut çalışmaların sonuçları ile karşılaştırılmıştır.

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Scutorientalin D, a neo-clerodane diterpenoid from Scutellaria orientalis subsp. pinnatifida

Cited by 25 publications

References 18 publications

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

The Enantiomeric Scaffold Approach to Highly Functionalized 1-Oxadecalines: Enantio- and Regiocontrolled [4 + 2] Cycloadditions of 5-Alkenyl-η³-Pyranylmolybdenum Complexes

Chemical Composition of the Essential Oil of Scutellaria orientalis L. subsp. virens (Boiss. Kotschy) J. R. Edm. from Turkey

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Scutorientalin D, a neo-clerodane diterpenoid from Scutellaria orientalis subsp. pinnatifida

Cited by 25 publications

References 18 publications

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

The Enantiomeric Scaffold Approach to Highly Functionalized 1-Oxadecalines: Enantio- and Regiocontrolled [4 + 2] Cycloadditions of 5-Alkenyl-η3-Pyranylmolybdenum Complexes

Chemical Composition of the Essential Oil of Scutellaria orientalis L. subsp. virens (Boiss. Kotschy) J. R. Edm. from Turkey

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The Enantiomeric Scaffold Approach to Highly Functionalized 1-Oxadecalines: Enantio- and Regiocontrolled [4 + 2] Cycloadditions of 5-Alkenyl-η³-Pyranylmolybdenum Complexes