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Lewis Acid-mediated Diastereoselective Synthesis of Medium-sized Cyclic Ethers and Studies Towards the Synthesis of Plakortolide E and 6-Epiplakortolide E
Başlık:
Lewis Acid-mediated Diastereoselective Synthesis of Medium-sized Cyclic Ethers and Studies Towards the Synthesis of Plakortolide E and 6-Epiplakortolide E
Yazar:
Tomaine, Anthony J., author.
ISBN:
9780438018372
Yazar Ek Girişi:
Fiziksel Tanımlama:
1 electronic resource (243 pages)
Genel Not:
Source: Dissertation Abstracts International, Volume: 79-10(E), Section: B.
Advisors: Arun K. Ghosh Committee members: Corey Thompson; Christopher Uyeda; Alexander Wei.
Özet:
The Lewis acid-mediated synthesis of medium-sized cyclic ethers has been achieved in a diastereoselective manner. Using TMSOTf or BF3•OEt 2, we developed a novel protocol for the intermolecular synthesis of eight-membered cyclic ethers (oxocenes) via Prins-type cyclization. This methodology displays a unique approach towards 2,4,8-trisubstiituted oxocene cores, with good yields and excellent diastereoselectivity. We have also expanded this protocol to show applicability towards the synthesis of seven-membered rings (oxepines and oxepanes).
Progress studies towards the synthesis of plakortolide E and 6-epiplakortolide E are described. Featuring a bicyclic peroxylactone, these compounds are of interest due to their potential antimalarial activity. A key step in these syntheses features a diastereoselective [4+2] cycloaddition with singlet oxygen, under photosensitized conditions.
Notlar:
School code: 0183
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Yer Numarası | Demirbaş Numarası | Shelf Location | Lokasyon / Statüsü / İade Tarihi |
---|---|---|---|
XX(680236.1) | 680236-1001 | Proquest E-Tez Koleksiyonu | Arıyor... |
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