Current Trends in Organic Synthesis. Proceedings of the by Hitosi Nozaki (Eds.)

By Hitosi Nozaki (Eds.)

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7% Thus, the S enantiomer of ketone 18 must react much faster with (S)- 4 2 than with O OHH 0 ° OSM IE 2. , kinetic resolution is operating. Since both reactants are racemic, the kinetic resolution is mutual, each enantiomer of 18 selecting the enantiomer of a-phenylpropionaldehyde with which it reacts more rapidly. This interesting behavior turns out to be a consequence of double stereodifferentiation. , eq 3 9 ) . °, OH 0 0 s i M e 3 C H ° •8 If we ignore the four threo OH 0 OSiMe 1 4 2 ' 3 >95% 0SiMe 3 <5% diastereomers that might have been formed from the reaction of racemic 18 with racemic a-phenylpropionaldehyde, we are left with the four erythro isomers 19-22.

4 Its importance in organic chemistry has certainly not gone unrecognized; indeed, it is the only method to which an entire volume of Organic Reactions has been d e v o t e d . 45 Yet, the casual reader of the chemical literature cannot help but notice that the aldol condensation is undergoing a renaissance. The special attention that has been given to the reaction during the last five years has been inspired in part by the hypothesis that it might provide a simple, direct solution to the stereochemical problem in the synthesis of molecules such as 1.

J. , New York, 1968. in press. 43 STUDIES DIRECTED TOWARDS VERRUCARINS: A SYNTHESIS OF VERRUGAROL. A N APPROACH TO VERRUCARIN A Barry M. Trost, Patrick G. McDougal and James H. Rigby McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin, 1101 UNIVERSITY AVENUE, Madison, WI 53706, USA A b s t r a c t - An a p p r o a c h t o v e r r u c a r i n A e n v i s i o n s d i s s e c t i o n i n t o v e r r u c a r o l , v e r r u c a r i n i c a c i d , and a d i f f e r e n t i a t e d jL,j£-muconate• A s t r a t e g y embodying t h e c o n c e p t s of g e m i n a l a l k y l a t i o n v i a c y c l o b u t a n o n e s and m o d i f i c a t i o n of o x i d a t i o n l e v e l v i a s u l f e n y l a t i o n r e a c t i o n s g e n e r a t e s a s e c o d e r i v a t i v e of v e r r u c a r o l .

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