A Useful Preparation of L- ( S ) -Glyceraldehyde Acetonide

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Abstract
In our current synthetic work directed toward spiroketal containing natural products, we needed to have access to (S)-glyceraldehyde acetonide in pure form. While Baer and Fischer described a preparation of this material in 1939 by a route analogous to that developed for (R)-glyceraldehyde acetonide, the use of unnatural L-mannitol is required.' More recently, Jung and Shaw have developed an expedient synthesis of (R)- glycerol acetonide from ascorbic acid which passes through (s)-g1yceraldehyde acetonide.2 This unstable aldehyde was not isolated, but was reduced directly to the alcohol. Additionally, Takano c.e.have reported a modification of the ascorbic acid route, but this procedure also proceeds directly to the alcoh0l.3 Since attempts in our hands to modify the JUng procedure so as to procure the aldehyde itself led to poor yields of impure material, we were forced to develop an alternate route.