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A Concise and Convergent Total Synthesis of Two Novel Cytotoxic Hydroquinones, Lanneaquinol and ( R )‐2′‐Hydroxylanneaquinol
Author(s) -
Subba Reddy Basireddy V.,
Anusha Bheemreddy,
Subba Reddy Ummareddy V.,
Yadav Jhillu S.,
Suresh Reddy Cirandur
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300066
Subject(s) - chemistry , hydroquinone , stereocenter , enantioselective synthesis , hydroxylation , total synthesis , stereochemistry , cyclohexane , alkylation , aldehyde , cytotoxic t cell , organic chemistry , catalysis , biochemistry , in vitro , enzyme
A short and efficient approach for the total synthesis of two novel cytotoxic hydroquinones, lanneaquinol ( 1 ) and ( R )‐2′‐hydroxylanneaquinol ( 2 ) isolated from the organic extract of the plant Lannea welwitschii , has been developed. Enantioselective organocatalytic McMillan hydroxylation has been successfully utilized for the creation of the stereogenic center bearing the OH group of ( R )‐2′‐hydroxylanneaquinol ( 2 ). The hydroquinone core was constructed through the alkylation of cyclohexane‐1,4‐dione with a corresponding aldehyde. Both hydroquinone natural products can be synthesized by a mere change in the synthetic strategy.