Synlett 2013; 24(15): 1915-1920
DOI: 10.1055/s-0033-1338974
letter
© Georg Thieme Verlag Stuttgart · New York

Toward the Total Synthesis of Divergolides C and D

Anastasia Hager
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   eMail: dirk.trauner@lmu.de
,
Christian A. Kuttruff
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   eMail: dirk.trauner@lmu.de
,
Dominik Hager
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   eMail: dirk.trauner@lmu.de
,
Daniel W. Terwilliger
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   eMail: dirk.trauner@lmu.de
,
Dirk Trauner*
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   eMail: dirk.trauner@lmu.de
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Publikationsverlauf

Received: 16. Juni 2013

Accepted: 25. Juni 2013

Publikationsdatum:
21. August 2013 (online)


Abstract

The divergolides are a family of structurally unprecedented ansa macrocycles. We describe a synthetic strategy toward divergolides C and D that hinges on the biomimetic diversification of a common intermediate. An advanced precursor that incorporates all the carbon atoms of divergolide C and D is presented, and atrop­isomerism in a sterically crowded acyl naphthalene is studied.

Supporting Information