Tetrahedron p. 1983 - 2004 (1997)
Update date:2022-08-04
Topics: Derivatives Optically active Preparation Experimental
Curran, Timothy T.
Hay, David A.
Koegel, Christopher P.
Evans, Jonathan C.
The preparation and enzymatic resolution of several cis-mono-4-O-protected-2-cyclopenten-1,4-diols are described. The process starts with inexpensive furfuryl alcohol and lends itself to the preparation of multigram quantities of various protected, optically active 2-cyclopenten-1,4-diol derivatives. Stereoselective reduction of 4-O-protected-2-cyclopentenone to the cis-mono-O-protected-2-cyclopenten-1,4-diol using LiAlH4/LiI or Red-Al/NaI is described. Subsequent pancreatin-promoted, stereoselective acylation was conducted on these cis-(+/-)-mono-O-protected-cyclopenten-1,4-diols to afford the corresponding alcohols and acetates in moderate to excellent enantioselectivities.
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