Total synthesis and biological evaluation of C-nor-D-homo Steroids

C-nor-D-同型类固醇的全合成及生物学评价

• 批准号: 268346890
• 负责人: Professor Dr. Athanassios Giannis
• 金额: --
• 依托单位: Institut für Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2014
• 资助国家: 德国
• 起止时间: 2013-12-31 至 2017-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/268346890?language=en
• 关键词: Total; synthesis; biological; evaluation; nor

C-nor-D-homo steroids (6-6-5-6 annulated systems) are natural products with interesting biological properties ranging from anti-tumoral to anti-diabetic activities. Despite of their importance in biology and medicine only a few synthetic entries to this steroids were described in the literature. In the frame of this proposal a general entry will be established. Starting from (-)-citronellal and the readily available (+)-Wieland-Miescher ketone, in a convergent approach, an open chain precursor will be synthesized which in a subsequent reaction, using the Nazarov cyclisation as a key step, will be transformed in one step to the C-nor-D-homo steroid. Our efforts will open the way to a general entry to this class of steroids and their non natural analogs. The synthesized compounds will be biologically evaluated using the Gli-reporter assay.

C-nor-D-homo甾体（6-6-5-6环状系统）是具有从抗肿瘤到抗糖尿病活性的有趣生物学性质的天然产物。尽管它们在生物学和医学上的重要性，但文献中仅描述了这种类固醇的少数合成条目。在本提案的框架内，将建立一个通用条目。从（-）-香茅醛和容易获得的（+）-Wieland-Miescher酮开始，在收敛方法中，将合成开链前体，其在随后的反应中，使用Nazarov环化作为关键步骤，将在一个步骤中转化为C-nor-D-高甾体。我们的努力将开辟一条道路，一般进入这类类固醇及其非天然类似物。将使用Gli报告基因测定法对合成的化合物进行生物学评价。

项目成果

Synthesis of C-Nor-D-homo-steroidal Alkaloids and Their Derivatives

C-正-D-同甾体生物碱及其衍生物的合成

• DOI: 10.1055/s-0036-1591965
• 发表时间: 2018
• 期刊: Synthesis
• 作者: F. Mousavizadeh;D. Meyer;A. Giannis;Synthesis

Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids.

• DOI: 10.1002/chem.201701008
• 发表时间: 2017-04
• 期刊: Chemistry
• 作者: J. Krieger;Toni Smeilus;Oliver Schackow;A. Giannis