The synthesis of biologically active steroids
Başlık çevirisi mevcut değil.
- Tez No: 400525
- Danışmanlar: DR. R. JAMES HANSON
- Tez Türü: Doktora
- Konular: Fizik ve Fizik Mühendisliği, Kimya, Çevre Mühendisliği, Physics and Physics Engineering, Chemistry, Environmental Engineering
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 1999
- Dil: İngilizce
- Üniversite: University of Sussex
- Enstitü: Yurtdışı Enstitü
- Ana Bilim Dalı: Fizikokimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 247
Özet
.
Özet (Çeviri)
The first chapter reviews the existing literature on the viridin family of steroidal antibiotics. The synthesis of a C-4:C-6 furano-steroid analogue of the demethoxyviridin family of antibiotics by the base-catalysed cyclisation of 6ot-acetoxyandrost-4-ene-3517-dione is described in chapter 2. Chemical studies on demethoxyviridin using materials biosynthesised from Nodulosporium hinmdeum 214826 is also described. Chapter 3 describes the synthesis of 4~chloroandrosta-3,5-diene-7,17-dione and the corresponding 17p-acetate as potential inhibitors for the aromatase enzyme system. The action of Jones' reagent (chromium trioxide in sulfuric acid and water) and m-chloroperbenzoic acid on dienes and trienes is examined in chapter 4. The chromic acid oxidation of steroidal 2,4- and 3,5-dienes and 2,4,6-trienes has been shown to take place at the secondary termini of the alkenes rather than at the allylic positions and has been rationalised in terms of a sequence of l:4-additions of chromic acid. The epoxidation of androsta-4,6-diene with m-chloroperbenzoic acid gave the 4p,5p;6a,7a-diepoxide whose stereochemistry can be rationalised in terms of the directing effect of one epoxide on the facial selectivity of the second epoxidation. The epoxidation of 6p-acetoxyandrosta-2,4-diene-17-one, 6p-acetoxypregna~2,4-diene-20-one and the corresponding 6-ketones with m-chloroperbenzoic acid afforded, unexpectedly, the 4a,5a-monoepoxides which might bind to a glutamate residue in the aromatase enzyme system and act as irreversible inhibitors. The stereochemistry of methanolysis of steroidal 2,3-epoxides and 4p,5p:6ot,7a-diepoxides catalysed by tetracyanoethylene (TCNE) is examined in chapter 5. The reaction of 17p-acetoxy-4p,5p;6a,7ct-diepoxyandrostane with TCNE in methanol afforded 17p-acetoxy-4cx,7a-oxido-5p-hydroxy-6p-methoxyandrostane in which the methanolysis product of the 6oc,7a-epoxide has participated in the cleavage of the 4(3,5p-epoxide. The TCNE catalysed methanolysis of androstane-2,3-epoxides proceeds normally without giving products arising from the transannular participation of a 5a,6a-epoxide, a 5a-hydroxyl group or a 5(6)-ene. The assignments of the 13C NMR spectra for some of the compounds described in the thesis are given in the appendix A.
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