Medium-ring 1,5-dienes. Part II. The radical and electrophile-induced cyclisation of germacra-1(10),4,7(11)-triene

Brown, Elsa Barkley; Sam, Teng W.; Sutherland, J. K.; Torre, A. De Ita

doi:10.1039/p19750002326

Cited by 27 publications

(11 citation statements)

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“…The transannular cyclization of germacrone via oxymercuriation-demercuriation, in contrast, forms mainly trans-eudesmane-type products (Scheme 16) [54] . These results were expected on the basis of the mechanism proposed by Sutherland [52,55] (Scheme 17). The attack of the mercuric acetate takes place preferentially on the 1,10 double bond, forming a mercurinium cation.…”

supporting

confidence: 75%

Germacrone: Occurrence, Synthesis, Chemical Transformations and Biological Properties

Barrero

Herrador

Arteaga

et al. 2008

Natural Product Communications

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This paper is dedicated to Professor Pedro Joseph-Nathan for his 65 th birthday. Germacrone (1) forms part of a great number of essential oils, in some of them comprising more than 20% of the total oil. This compound presents a wide range of biological activities (CNS depressant, antiinflammatory, antiulcer, antifeedant, antibacterial, antifungal, antitumor, antitussive, vasodilator, choleretic, hepatoprotector), which are analyzed. The chemical reactivity of germacrone, including cyclization reactions, and complete synthesis are presented.

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supporting

confidence: 75%

Germacrone: Occurrence, Synthesis, Chemical Transformations and Biological Properties

Barrero

Herrador

Arteaga

et al. 2008

Natural Product Communications

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“…Germacrene B (1) was synthesized from germacrone (2) in a manner similar to that reported (Brown et al, 1975).…”

Section: Resultsmentioning

confidence: 99%

HPLC isolation of the sesquiterpene hydrocarbon germacrene B from lime peel oil and its characterization as an important flavor impact constituent

Clark¹,

Chamblee²,

Iacobucci³

1987

J. Agric. Food Chem.

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“…Transannular cyclizations have also been reported with 1,5-dienes, as illustrated by the cyclization of germacra-1(10),4,6(11)-triene 130 upon irradiation in the presence of thiophenol or diphenyl disulfide (Scheme ) …”

Section: Addition Of Thiols To Cc Bondsmentioning

confidence: 97%

Thiyl Radicals in Organic Synthesis

et al. 2014

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Medium-ring 1,5-dienes. Part II. The radical and electrophile-induced cyclisation of germacra-1(10),4,7(11)-triene

Cited by 27 publications

References 0 publications

Germacrone: Occurrence, Synthesis, Chemical Transformations and Biological Properties

Germacrone: Occurrence, Synthesis, Chemical Transformations and Biological Properties

HPLC isolation of the sesquiterpene hydrocarbon germacrene B from lime peel oil and its characterization as an important flavor impact constituent

Thiyl Radicals in Organic Synthesis

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