Concise Total Synthesis of (+)-Atlanticone C

被引:10
作者
Proessdorf, Johanna
Zech, Andreas
Jandl, Christian
Bach, Thorsten [1 ]
机构
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
关键词
asymmetric synthesis; total synthesis; photocycloaddition; chiral resolution; protoilludanes; atlanticone C; ABSOLUTE-CONFIGURATION; COMPLEX; ASSIGNMENT; REDUCTION; OXIDATION; ALCOHOLS; ACID;
D O I
10.1055/s-0040-1707215
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey-Bakshi-Shibata reduction permitted a catalytic chiral reso-lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (-)-atlanticone C was thereby determined.
引用
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页码:1598 / 1602
页数:5
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