A Concise and Convergent Total Synthesis of Two Novel Cytotoxic Hydroquinones, Lanneaquinol and ( R )‐2′‐Hydroxylanneaquinol | Zendy

Subba Reddy Basireddy V. | Zendy; Anusha Bheemreddy | Zendy; Subba Reddy Ummareddy V. | Zendy; Yadav Jhillu S. | Zendy; Suresh Reddy Cirandur | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research