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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 %.