Premium
Asymmetric Synthesis of (+)‐Tanikolide and the β‐Methyl‐Substituted Analogues of (+)‐Tanikolide and (–)‐Malyngolide
Author(s) -
Doran Robert,
Duggan Lesley,
Singh Surrendra,
Duffy Colm D.,
Guiry Patrick J.
Publication year - 2011
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.201101190
Subject(s) - chemistry , intramolecular force , natural product , enantioselective synthesis , stereochemistry , yield (engineering) , lactone , brine shrimp , antifungal , catalysis , combinatorial chemistry , organic chemistry , medicine , materials science , dermatology , metallurgy , traditional medicine
The δ‐lactone‐containing natural product (+)‐tanikolide, a brine shrimp toxin and antifungal compound, was synthesized in nine steps with an overall yield of 26.4 % by employing Sharpless asymmetric epoxidation and ZrCl 4 ‐catalyzed intramolecular acetalization as the key steps. The novel β‐methyl‐substituted analogues of (+)‐tanikolide and(–)‐malyngolide have also been prepared by using the same asymmetric synthetic approach.