An enantioselective route to the hydroxyfuran acetal substructure 36 of azadirachtin is described. The enantiopure key intermediate 29 was obtained in both absolute configurations by a kinetic resolution experiment, making use of an optical pure cyclopentadiene. After protection of the cyclopentenone double bond a highly diastereoselective reduction—cyclisation sequence, that may mimic the biogenetic pathway, afforded the tricyclic framework of the target molecule. Chirality 9:454–458, 1997.
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Schlesiger et al. (1997) studied this question.
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