Enantioselective Synthesis of (−)‐Exiguolide by Iterative Stereoselective Dioxinone‐Directed Prins Cyclizations | Zendy

Crane Erika A. | Zendy; Zabawa Thomas P. | Zendy; Farmer Rebecca L. | Zendy; Scheidt Karl A. | Zendy

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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.

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