Premium
Enantioselective Synthesis of (−)‐Exiguolide by Iterative Stereoselective Dioxinone‐Directed Prins Cyclizations
Author(s) -
Crane Erika A.,
Zabawa Thomas P.,
Farmer Rebecca L.,
Scheidt Karl A.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201102790
Subject(s) - tetrahydropyran , prins reaction , enantioselective synthesis , aldehyde , chemistry , stereoselectivity , computer science , stereochemistry , combinatorial chemistry , information retrieval , organic chemistry , catalysis , ring (chemistry)
Three become one : The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (−)‐Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z ‐enoate geometry are both necessary for this cytotoxicity.