Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans.
نویسندگان
چکیده
A simple and practical method for synthesis of the D-ring modified steroidal dienamides (4a-k) from the steroidal α,α-dicyanoalkene 3 and aldehydes via vinylogous aldol reaction was first reported. By using NaOAc as a base, the desired products were obtained in moderate to good yields in ethanol under mild conditions. All the synthesized steroidal dienamides are new and are currently being evaluated for their biological activities.
منابع مشابه
Synthesis of Novel 17-Oxo-17a-Aza-D-Homo-3, 5-Seco-Steroids as Potential 5α-Reductase Inhibitors
Benign prostatic hyperplasia (BPH) is a non-malignant enlargement of the prostate gland. Itis a leading disorder of the elderly male population. Excessive production of dihydrotestosteronehas been implicated in this pathological condition. Steroidal 5α-reductase is a membrane boundNADPH dependent enzyme which is responsible for the conversion of testosterone (T) todihydrotestosterone (DHT). The...
متن کاملSolvent-Free Multicomponent Reactions of Dithiocarbamates, Activated Acetylenes and Isocyanides
An efficient method to synthesis the 2H-pyrans using three component reactions of dithiocarbamats, activated acetylenes and isocyanides in water as the solvent is described. In these reactions, synthesis of 2H-pyrans is possible based on the one-pot reaction and without using any catalyst. The mild reaction conditions and high yields of the products exhibit synthetic advantage of these methods.
متن کاملEnantioselective total synthesis of marine diterpenoid clavulactone.
The key steps in the synthesis of clavulactone are formation of an enantiopure cyclopentane precursor by epoxide rearrangement and intramolecular carbonyl-ene reaction, construction of the 3,4-dihydro-2H-pyran ring by intermolecular hetero-Diels-Alder reaction, closure of the eleven-membered ring, and finally generation of the lactone functionality by chemoselective allylic C(sp(3))-H oxidation.
متن کاملFacile one-pot multicomponent synthesis of 2-amino-6-(2-oxo-2H-chromen- 3-yl)-4-arylpyridine-3-carbonitriles using Brønsted acidic ionic liquid as catalyst under solvent-free conditions
A series of 2-amino pyridine-3-carbinitrile derivatives incorporated coumarin moiety has developed via multicomponent condensation of 3-acetyl-2H-chromen-2-one, arylaldehydes, malononitrile and ammonium acetate utilizing Brønsted acidic ionic liquid, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate as catalyst under solvent-free conditions. Good yields, short reaction times, straig...
متن کاملBenign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction
An efficient construction of 2-(N-arylamino)benzaldehydes and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives starting from 2- hydroxybenzaldehydes has been developed. The synthesis of N-aryl-3,10-dihydroacridin-1(2H)-ones is based on the Knoevenagel condensation of dimedone to various 2-(N-arylamino)benzaldehydes, followed by an intramolecular enamination in the presence of 20 mol% of nanocry...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Steroids
دوره 78 5 شماره
صفحات -
تاریخ انتشار 2013