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Studies toward the Total Synthesis of Cryptotrione
Başlık:
Studies toward the Total Synthesis of Cryptotrione
Yazar:
Lyu, Maoyun, author.
ISBN:
9780438147829
Yazar Ek Girişi:
Fiziksel Tanımlama:
1 electronic resource (333 pages)
Genel Not:
Source: Dissertation Abstracts International, Volume: 79-11(E), Section: B.
Advisors: Nai Ching Wong.
Özet:
Cryptotrione, a novel C35-terpene with an unprecedented skeleton possessing an abietane diterpene together with a unique spiro-bicyclo[3.1.0]hexane sesquiterpene, was isolated from the bark of Cryptomeria japonica in 2010.
The intriguing structure and potential bioactivities have attracted our attention. Since there were no total syntheses reported, we would like to conduct synthetic studies towards the total synthesis of cryptotrione. From commercially available homoveratric acid, the key intermediate 193 with all cyclic backbone of cryptotrione was constructed successfully in 25 longest linear steps.
The key feature of this synthetic work included: (1) The first discovery of a gold(I) catalyzed intramolecular cascade reaction of 1,5-enyne benzyl ether triggered by a 1,6-hydride transfer/cyclization. (2) A substrate controlled diastereoselective formation of bicyclo[3.1.0] moiety by platinum (IV) catalyzed 1,5-enyne isomerization was successfully disclosed; (3) The construction of the abietane-type skeleton of cryptotrione by utilizing a Lewis acid induced diastereoselective polyene cyclizaiton. It is possible for us to develop the divergent synthesis of other members of cryptotrione family employing this strategy.
Notlar:
School code: 1307
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Yer Numarası | Demirbaş Numarası | Shelf Location | Lokasyon / Statüsü / İade Tarihi |
---|---|---|---|
XX(697028.1) | 697028-1001 | Proquest E-Tez Koleksiyonu | Arıyor... |
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