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Literature DB >> 12010033

Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).

Ruichao Shen¹, Cheng Ting Lin, John A Porco.

Abstract

The total synthesis and stereochemical assignment of the potent antitumor macrolide lobatamide C is reported. The synthesis involves Cu(I)-mediated enamide formation and Na(2)CO(3)-mediated esterification of a beta-hydroxy acid and a salicylate cyanomethyl ester. Macrolactonization was accomplished using a Mitsunobu protocol. The stereochemical assignment of lobatamide C was achieved by Mosher ester analysis and comparison with prepared stereoisomers.

Entities: Chemical

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Year: 2002 PMID： 12010033 DOI： 10.1021/ja026025a

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

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2. Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

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3. Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

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4. Studies on the Synthesis of Reidispongiolide A: Stereoselective Synthesis of the C(22)-C(36) Fragment.

Authors: Maben Ying; William R Roush
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5. Total synthesis of neopeltolide and analogs.

Authors: Yubo Cui; Wangyang Tu; Paul E Floreancig
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

6. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors: John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal: Org Lett Date: 2009-08-20 Impact factor: 6.005

Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).

1. A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

2. Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

3. Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

4. Studies on the Synthesis of Reidispongiolide A: Stereoselective Synthesis of the C(22)-C(36) Fragment.

5. Total synthesis of neopeltolide and analogs.

6. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

7. Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

8. Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

9. A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

10. Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.