Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4796-4808 ◽  
Author(s):  
Leslie Aldrich ◽  
Qiwen Gao ◽  
Lianyan Xu ◽  
Vincent Parise ◽  
Yash Mehta
Keyword(s):  
Biological Evaluation ◽  
Enantioselective Synthesis ◽  
Allylic Alcohol ◽  
Nucleophilic Aromatic Substitution ◽  
Asymmetric Epoxidation ◽  
Aromatic Substitution ◽  
Chemical Library ◽  
Epoxy Alcohols ◽  
Sharpless Asymmetric Epoxidation

A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.

A short enantioselective synthesis of 3-epi-jaspine B and (+)-oxybiotin via an intramolecular tandem desilylation oxa-Michael addition strategy

RSC Advances ◽  
2014 ◽  
Vol 4 (91) ◽  
pp. 49770-49774 ◽  
Author(s):  
Anil M. Shelke ◽  
Varun Rawat ◽  
Arumugam Sudalai ◽  
Gurunath Suryavanshi
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Asymmetric Epoxidation ◽  
Michael Addition Reaction ◽  
New Synthesis ◽  
Sharpless Asymmetric Epoxidation ◽  
Jaspine B

A new synthesis of cytotoxic 3-epi-jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee) is described starting from cis-2-butene-1,4-diol. The key reactions employed in the synthesis are Sharpless asymmetric epoxidation and a novel tandem desilylation-oxa Michael addition reaction.

scholarly journals Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution

2018 ◽  
Vol 20 (7) ◽  
pp. 2037-2041 ◽  
Author(s):  
Mariel M. Cardenas ◽  
Sean T. Toenjes ◽  
Christopher J. Nalbandian ◽  
Jeffrey L. Gustafson
Keyword(s):  
Enantioselective Synthesis ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals A Facile Stereoselective Total Synthesis of (R)-Rugulactone

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
B. Narasimha Reddy ◽  
R. P. Singh
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Cross Metathesis ◽  
Hydride Reduction ◽  
Novel Synthesis ◽  
Metathesis Reactions ◽  
Epoxy Alcohols ◽  
Allyl Alcohols ◽  
Sharpless Asymmetric Epoxidation

An efficient and novel synthesis of (R)-rugulactone has been achieved employing Sharpless asymmetric epoxidation of allyl alcohols followed by selective hydride reduction of epoxy alcohols and olefin cross metathesis reactions.

Sign in / Sign up

Export Citation Format

Share Document