Convergent Total Synthesis of (+)-Ophiobolin A

被引:48
作者
Tsuna, Kazuhiro [1 ]
Noguchi, Naoyoshi [1 ]
Nakada, Masahisa [1 ]
机构
[1] Waseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
关键词
cross-coupling; natural products; ring-closing metathesis; sesterterpenes; total synthesis; RING-CLOSING METATHESIS; NATURALLY-OCCURRING CYCLOOCTANOIDS; SILYLOXY-COPE REARRANGEMENT; OPHIOBOLANE SESTERTERPENES; CEROPLASTIN NUCLEUS; 8-MEMBERED RINGS; CEPHALONIC ACID; BUILDING-BLOCK; FACILE ROUTES; ALBOLIC ACID;
D O I
10.1002/anie.201104447
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
At long last: The enantioselective total synthesis of the title compound, which was isolated in 1958, proceeds by a convergent approach. The assembly of the C,D-ring fragment and the A-ring fragment of the core structure is achieved by employing a Reformatsky-type reaction. The eight-membered carbocyclic B ring is efficiently constructed by a challenging ring-closing metathesis (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9452 / 9455
页数:4
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