Abstract
Aldol reactions of methyl 2-methoxypropanoate ( 4), the corresponding ester of 2-methoxypropanoic acid with 4-methyl-2,6-di-( tert-butyl)phenol ( 13), and silylketene acetals 14 and 15 with ( S)-2-(phenylmethoxy)propanal ( 17) have been investigated. The lithium enolate of 4 reacts with 17 to give primarily β-hydroxy ester 18a. If the reaction is carried out with the bis-silylketene acetal 14 under the influence of stannic chloride, β-hydroxy acid 20c is produced. Compound 20c is cleanly inverted, via the β-lactone 26, to provide β-hydroxy acid 19c. Compound 18a has been converted into l-cladinose by the sequence of steps: 18a→35→39→40→41→42→1.
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