Total synthesis of 14β-fluorosteroids via a transannular DielsAlder reaction-Reference-Cited by-同舟云学术

Total synthesis of 14β-fluorosteroids via a transannular DielsAlder reaction

Published:2006-01-01 Issue:1 Volume:84 Page:29-48
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Beaubien Sylvie,Deslongchamps Pierre

Abstract

14β-Fluorosteroids 3 and 4 were synthesized to give a new class of unnatural cardenolides. The total synthesis of racemic 14β-fluorosteroids was accomplished using a highly diastereoselective transannular DielsAlder reaction on a trans-cis-cis macrocyclic triene. The α-fluoro analog 4 provided a comparable inhibitory activity to natural digitoxigenin 1.Key words: fluorosteroid, bioisostere, cardiovascular diseases, transannular DielsAlder reaction (TADA), macrocyclization.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v05-259

Reference27 articles.

1. A New Approach to the Design of Novel Inhibitors of Na+,K+-ATPase: 17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

2. The transannular Diels–Alder strategy: applications to total synthesis

3. STUDIES IN OZONOLYSIS. III. CLEAVAGE OF ALKENE OZONIDES WITH LITHIUM ALUMINUM HYDRIDE

Cited by 11 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon;The Journal of Organic Chemistry;2023-10-12

2. An Asymmetric Total Synthesis of Picrotoxinin through a Mizoroki–Heck Reaction;Synlett;2022-11-17

3. Catalytic Cyanation Using CO2 and NH3;Chem;2018-12

4. Tandem aldol condensation-Diels–Alder-aromatization sequence of reactions: a new pathway for the synthesis of 2-tetralone derivatives;Canadian Journal of Chemistry;2016-09

5. The Diels–Alder Reaction in Steroid Synthesis;Synthesis;2014-11-17