Flexible Approach to (5 Z ,9 Z )‐Dienoic Fatty Acids Relevant to the Synthesis of Demospongic Acids and Related Natural Products | Zendy

Adrian Juliane | Zendy; Stark Christian B. W. | Zendy

Premium

Flexible Approach to (5 Z ,9 Z )‐Dienoic Fatty Acids Relevant to the Synthesis of Demospongic Acids and Related Natural Products

Author(s) -

Adrian Juliane,

Stark Christian B. W.

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600746

Subject(s) - chemistry , hydroboration , yield (engineering) , alkynylation , total synthesis , organic chemistry , alcohol , combinatorial chemistry , stereochemistry , catalysis , materials science , metallurgy

A flexible and efficient synthesis of the potent human topoisomerase inhibitor (5 Z ,9 Z )‐eicosa‐5,9‐dienoic acid was explored; the presented method represents a generally applicable approach towards demospongic acids and related natural products. Key steps of the synthesis involve chemoselective hydroboration, Corey–Fuchs alkynylation, Z ‐selective Lindlar reduction, tetrapropylammonium perruthenate catalyzed direct oxidation of a primary alcohol to the corresponding acid, and Arndt–Eistert homologation. Thus, the total synthesis of (5 Z ,9 Z )‐eicosa‐5,9‐dienoic acid was achieved in 10 steps in an overall yield of 20 %.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research