- Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion
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We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP1B inhibitory activity, in ten steps. Over the course of this study, two key methodological advances were made: a cost-effective procedure for ketone α,β-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2H-pyran to a pyridine. These studies have led to the structural revision of two members of this family.
- Schuppe, Alexander W.,Zhao, Yizhou,Liu, Yannan,Newhouse, Timothy R.
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supporting information
p. 9191 - 9196
(2019/06/17)
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- Synthesis of dl-pyroangolensolide
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A diastereoselective synthesis of dl-pyroangolensolide has been accomplished starting from 2,6-dimethylcyclohexenone in four steps in 62% yield. The key step involves an absolute threo selective aldol reaction.
- Fernandez-Mateos, Alfonso,Benito, Manuel Grande,Coca, Gustavo Pascual,Gonzalez, Rosa Rubio,Hernandez, Carolina Tapia
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p. 7521 - 7526
(2007/10/02)
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- Synthesis of Limonoid Model Insect Antifeedants through Stereoselective Aldol Addition Reactions
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The aldol condensation of 3-furaldehyde and enol silanes or enolates (Li, Mg, and Ti) of 2,6-dimethyl- and 2,2,6-trimethylcyclohexanones has been investigated (Tables I, II and Chart II).The reaction of dimethyl enol silane 1 showed poor facial and diaste
- Mateos, Alfonso Fernandez,Blanco, Jesus Angel de la Fuente
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p. 7084 - 7092
(2007/10/02)
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- Synthetic Studies on Terpenoid Compounds. Part 14. Total Synthesis of Pyroangolensolide
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4.8-Dimethyl-1,4,5,6,7,7a-hexahydroinden-2-one (7), obtained by Wichterle annelation of 2,6-dimethylcyclohexanone, was converted into 1-hydroxy-5,8-dimethyl-1,7,8,9-tetrahydro-3H-2-benzopyran-3-one (26).Treatment of compound (26) with 3-lithiofuran afforded pyroangolensolide (1) together with its diastereomer (4).
- Tokoroyama, Takashi,Fukuyama, Yoshiyashu,Kotsuji, Yasuhito
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p. 445 - 450
(2007/10/02)
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- STUDIES TOWARDS THE TOTAL SYNTHESIS OF MEXICANOLIDE. STEREOSELECTIVE CONSTRUCTION OF THE CD RING SEGMENT FOR A CONVERGENT APPROACH
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The CD ring segment 18 required for a convergent approach towards the total synthesis of the limonoid mexicanolide (3) has been prepared in a highly stereoselective manner.
- Liu, Hsing-Jang,Dieck-Abularach, Teofilo
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p. 245 - 249
(2007/10/02)
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