The lithium enolate of the acetonide of (S,S)-dimethyl tartrate 5 was prepared by treatment with lithium diisopropylamide in the presence of 12-crown-4, and added to acetonylacetone 6; reaction of the product with acid gave a mixture of cyclised adducts from which a single diastereoisomer was isolated and shown to have a structure consistent with the core of squalestatin.
V. K. Aggarwal, M. F. Wang and A. Zaparucha, J. Chem. Soc., Chem. Commun., 1994, 87 DOI: 10.1039/C39940000087
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