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This paper deals with an approach to the enantioselective total synthesis of Lyngbyatoxin A, with focus on the stereocontrolled introduction of the quaternary stereogenic centre. The key step in the synthesis involves an enantiospecific Lewis-acid mediated rearrangement of chiral vinyl epoxides carrying a 7-substituted indole moiety.
The Peterson reaction between a series of 2-substituted 1-azabicyclo[2.2.2]octan-3-ones and 3-methyl-5-trimethylsilanylmethyl isoxazole (1) was explored. (Z)-Stereoselectivity was obtained with all 2-substituents, ranging from 65:35 for benzyl to 95:5 for phenylsulphanyl. Different bases were investigated, revealing that an organolithium base is necessary for the reaction to occur. A transition state...
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