Journal article
Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins
Tetrahedron Letters, Vol.45(32), pp.6147-6150
2004
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.
Details
- Title
- Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins
- Authors/Creators
- A.A. Birkbeck (Author/Creator)Z. Brkic (Author/Creator)R.G.F. Giles (Author/Creator)
- Publication Details
- Tetrahedron Letters, Vol.45(32), pp.6147-6150
- Publisher
- Elsevier BV
- Identifiers
- 991005544750307891
- Copyright
- © 2004 Elsevier Ltd.
- Murdoch Affiliation
- School of Mathematical and Physical Sciences
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 1 Clinical & Life Sciences
- 1.219 Cancer Drugs
- 1.219.1527 Naphthoquinone Derivatives
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry