Abstract
In a novel Michael-type reaction L-ascorbic acid ( 1 ) undergoes addition to acrolein to give the tricyclic hemiacetal lactone 3 . The constitution and relative configuration of 3 was studied by a combination of NMR and IR spectroscopy. Ultimately, the structure of 3 was determined by X-ray crystallography. The absolute stereochemistry follows from the known chirality of C-4 and C-5 of L-ascorbic acid. A mechanism for the reaction, including its steric course, is proposed. Methyl vinyl ketone reacts with 1 in a similar fashion to give diketo lactone derivative 4 , Upon the action of methanolic hydrogen chloride on 4 one anomer, the tricyclic methyl ketal lactone 5 , forms. Structure 5 is closely related to 3 . Synthetic and possible biological applications of the new reaction are discussed.
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