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Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins

Birkbeck, A.A., Brkic, Z. and Giles, R.G.F. (2004) Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins. Tetrahedron Letters, 45 (32). pp. 6147-6150.

Link to Published Version: http://dx.doi.org/10.1016/j.tetlet.2004.06.065
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Abstract

The enantiopure (1S,3S,4R)-, (1R,3S,4S)- and (1S,3S,4S)-3,4-dihydro-1,3-dimethyl-4-hydroxy-2-benzopyrans 16, 25 and 26 are prepared in two related reaction sequences, each in eight steps and good overall yield. The starting materials are 4-methoxyphenol 6 and (2S,1′R and 2S,1′S)-1′ ethoxyethoxypropanal 9, the latter providing the source of asymmetry from the chiral pool. The three key reactions involved in each sequence are either highly or completely diastereoselective.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Elsevier BV
Copyright: © 2004 Elsevier Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/35937
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