Download PDF
Synfacts 2011(11): 1160-1160  
DOI: 10.1055/s-0031-1289273
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Communiol E

Contributor(s): Steven V. Ley, Matthew O’Brien
S. Kobayashi*, T. Kinoshita, T. Kawamoto, M. Wada, H. Kuroda, A. Masuyama, I. Ryu
Osaka Prefecture University, Japan
Further Information

Publication History

Publication Date:
19 October 2011 (online)

    Permissions and Reprints

Significance

Communiol E is a bicyclic poly­ketide isolated from the coprophilous fungus Podospora communis, originally obtained from horse dung. Here an iodolactonization, followed by a recently developed radical carbonylation-­reduction reaction provide efficient access to the core of the molecule. An oxy-Favorskii reaction stereoselectively provides the tetrahydrofuran ring.