Merrilactone transannular aldol reaction

In a recent total synthesis of the novel neurotrophic agent merrilactone A (22, Scheme 4) by Inoue and Hirama [24], key intermediate 21 with the cis-bicyclo[3.3.0] octane framework embedded within the caged pentacycle 22 was elaborated from cyclobutane 18 by a sequence of RCM and immediate cleavage of the resulting bicyclic vicinal diol 19 to raeso-diketone 20. Cyclooctenedione 20 then underwent regioselective transannular aldol reaction at low temperature (LHMDS, THF, -100 °C) to produce a 3 1 mixture of isomers in 85% combined yield. The major isomer 21 with the required stereochemistry was then converted into the racemic natural compound ( )-22 in 19 steps. 

Scheme 4 A sequence of RCM-glycol cleavage-transannular aldol reaction in Inoue s total synthesis of merrilactone A (22) [24]...

SCHEME 20.20. The transannular aldol reaction in the synthesis of (+)-merrilactone A. 

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See also in sourсe #XX -- [ , ]

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