Tetrahedron p. 2855 - 2862 (1986)
Update date:2022-08-06
Topics:
Hoye, Thomas R.
Suhadolnik, Joseph C.
A complementary set of stereochemically controlled approaches to the preparation of twelve diastereomers of the bistetrahydrofurans 11 is described.The key transformation involves a series of nucleophilic displacement reactions within triepoxides 19 - the "end-to-end" triepoxide cascade reaction - which leads, presumably via 22 and 23, after acetylation to bistetrahydrofuran tetraacetates 24.The "inside-out cyclization of 30 exemplifies a useful variation with significant stereochemical consequences.The role of symmetry in these approaches is discussed.A general mathematical analysis for conceptualizing isomer distribution within multistep sequences is presented.
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