Synthetic potential of the PET-decarboxylation of ω-phthalimido carboxylic acids
Kramer, W., Griesbeck, A.G., Nerowski, F., and Oelgemoeller, M. (1998) Synthetic potential of the PET-decarboxylation of ω-phthalimido carboxylic acids. Journal of Information Recording, 24. pp. 81-85.
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Abstract
Photodecarboxylation of potassium salts of w-phthalimido alkanoates in water/acetone mixtures was used to synthesize medium- and large-ring compounds. An efficient synthesis of a benzopyrrolizidine from the corresponding glutamic monomethyl ester was developed. This product was transformed into functionalized pyrrolizidines 3 and 4 with high diastereoselectivity using acyliminium chemistry. Macrocyclic lactones 6, 9a were accessible from their acyclic precursors by the same procedure in high yields. A subsequent photoextrusion of carbon dioxide leading to spirocyclopropanes 11 was discovered in the case of the photolabile seven- and eight-membered macrolides 10a and 10b.
| Item ID: | 29901 |
|---|---|
| Item Type: | Article (Research - C1) |
| ISSN: | 1025-6008 |
| Keywords: | photoinduced electron transfer; photodcarboxylation; acyliminium cations; macrolides |
| Date Deposited: | 28 Oct 2013 02:51 |
| FoR Codes: | 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 60% 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 40% |
| SEO Codes: | 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100% |
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