Tetrahedron p. 3631 - 3658 (1996)
Update date:2022-08-03
Topics:
Binns, Falmai
Hayes, Roy
Hodgetts, Kevin J.
Saengchantara, Suthiweth T.
Wallace, Timothy W.
Wallis, Christopher J.
Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.
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