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Novel methods for the preparation of the indole phytoalexin rutalexin (8) in high yields are presented. The synthesis of rutalexin (8) was achieved from previously synthesized 9-tert-butoxycarbonyl-2-methoxy-4-oxo-[1,3]thiazino[6,5-b]indole (5) by its hydrolysis, methylation, and deprotection. A second method starting from 9-Boc-cyclobrassinin (9) involved oxidation, methylation, and deprotection.
Stereoselective synthesis of cruciferous indole phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(−)-enantiomer was achieved by spirocyclization of 1-methoxybrassinin in the presence of (+)- and (−)-menthol and subsequent oxidation of the obtained menthyl ethers. Methanolysis of menthyl ethers in the presence of TFA afforded (2R,3R)-(−)-1-methoxyspirobrassinol methyl ether as well...
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