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Synfacts 2011(12): 1265-1265
DOI: 10.1055/s-0031-1289342
DOI: 10.1055/s-0031-1289342
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Ophiobolin A
Contributor(s):Steven V. Ley, Sean NewtonK. Tsuna, N. Noguchi, M. Nakada*
Waseda University, Tokyo, Japan
Convergent Total Synthesis of (+)-Ophiobolin A
Angew. Chem. Int. Ed. 2011, 50: 9452-9455
Waseda University, Tokyo, Japan
Convergent Total Synthesis of (+)-Ophiobolin A
Angew. Chem. Int. Ed. 2011, 50: 9452-9455
Further Information
Publication History
Publication Date:
18 November 2011 (online)
Key words
Reformatsky reaction - sesterterpenes - ring-closing metathesis
Significance
(+)-Ophiobolin is a naturally occurring sesterterpene isolated from the pathogenic plant fungus Ophiobolus miyabeanus in 1958. It exhibits bioactivity against a range of nematodes, fungi, and bacteria. Herein, the first total synthesis of (+)-ophiobolin is reported.
Comment
This synthesis utilizes Utimoto’s conditions (Tetrahedron Lett. 1988, 29, 1041) for the Reformatsky-type coupling of α-bromo ketone C and aldehyde B in high yield. Stereoselective hydrogenation and methyl addition are utilized to install the stereocenters at C2 and C3 with excellent selectivity. A ring-closing metathesis is used to form the unsaturated eight-membered ring.