- Synthesis of a New Phorbazole and Its Derivatives
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Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.
- Muderawan, I Wayan,Loughlin, Wendy A.,Young, David J.
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p. 1395 - 1403
(2021/11/30)
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- Catalyst-Controlled Chemodivergent Reactions of 2-Pyrrolyl-α-diazo-β-ketoesters and Enol Ethers: Synthesis of 1,2-Dihydrofuran Acetals and Highly Substituted Indoles
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A catalyst-controlled, chemodivergent reaction of pyrrolyl-α-diazo-β-ketoesters with enol ethers is reported. While Cu(II) catalysts selectively promoted a [3 + 2] cycloaddition to provide pyrrolyl-substituted 2,3-dihydrofuran (DHF) acetals, dimeric Rh(II) catalysts afforded 6-hydroxyindole-7-carboxylates via an unreported [4 + 2] benzannulation. The choice of enol ether proved to be crucial in determining both regioselectivity and yield of the respective products (up to 91% yield for Cu(II) and 82% for Rh(II) catalysis). Furthermore, the DHF acetals were shown to serve as precursors to 7-hydroxyindole-6-carboxylates (isomeric to the indoles formed from Rh) and highly substituted furans in the presence of Lewis acids. Thus, from a common pyrrolyl-α-diazo-β-ketoester, up to three unique heterocyclic scaffolds can be achieved based on catalyst selection.
- France, Stefan,Guerra Faura, Gabriel,Nguyen, Tena
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supporting information
p. 10088 - 10104
(2021/07/31)
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- Investigations into the parallel synthesis of novel pyrrole-oxazole analogues of the insecticide pirate
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Investigations into the parallel synthesis of selected analogues of a structurally unique pyrrole-oxazole analogue of the pyrrole insecticide pirate, are reported. Acylaminoketone salts were obtained from ketobromides in moderate to high yields and excell
- Loughlin, Wendy A.,Henderson, Luke C.,Elson, Kathryn E.,Murphy, Michelle E.
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p. 1975 - 1980
(2007/10/03)
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- Synthesis of a novel pyrrole oxazole analogue of the insecticide pirate
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The pyrrole oxazole 4 is a novel analogue of the broad-spectrum insecticide and miticide pirate 2. The expedient synthesis of pyrrole oxazole 4 in six steps from pyrrole is reported using a synthetic route that could have potential for the solution-phase
- Loughlin, Wendy A.,Murphy, Michelle E.,Elson, Kathryn E.,Henderson, Luke C.
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p. 227 - 232
(2007/10/03)
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- Studies towards the synthesis of phorbazoles A-D: Formation of the pyrrole oxazole skeleton
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Synthetic approaches towards the synthesis of the pyrrole oxazole skeleton of phorbazoles A-D are described. An efficient synthesis of the pyrrole oxazole skeleton (19) from pyrrole and 4-methoxyacetophenone was developed. In the key step, cyclodehydratio
- Loughlin, Wendy A.,Muderawan, I. Wayan,McCleary, Michelle A.,Voller, Katie E.,King, Malcolm D.
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p. 231 - 234
(2007/10/03)
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