Hydrogenation Selectivity of the Bicyclo[4.4.0]decane Ring System of Valencanes

Sauer, Anne M.; Crowe, William E.; Henderson, Gregg; Laine, Roger A.

doi:10.1055/s-0029-1219206

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Cited by 2 publications

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Formation of Alkanes and Arenes by Reduction

Larock

Zhang

2017

Comprehensive Organic Transformations

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Cyclic Alkanes Arenes Alkenes Alkynes Organic Halides Amines and Derivatives Nitro Compounds Ethers Alcohols and Phenols Sulfur Compounds Selenium and Tellurium Compounds Aldehydes and Ketones Acetals Carboxylic Acids Acid Halides Anhydrides Esters and Lactones Nitriles Isonitriles

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Formation of Alkanes and Arenes by Reduction

Larock

Zhang

2017

Comprehensive Organic Transformations

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Total Synthesis and Biological Evaluation of Cell Adhesion Inhibitors Peribysin A and B: Structural Revision of Peribysin B

Kalmode¹,

Handore

Rajput

et al. 2018

Org. Lett.

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Total synthesis of potent cell-adhesion inhibitors peribysins A and B has been accomplished for the first time in racemic form. A Diels–Alder/aldol sequence to build the skeleton and decoration of the desired functionalities of the targeted natural products using highly stereoselective operations are the highlights. The structures of synthesized peribysins were fully characterized using spectral data and single-crystal X-ray analysis. Through this total synthesis, the initially proposed structure of peribysin B has been revised. Furthermore, the cell-adhesion inhibition potential of the scaffold (two peribysins + three analogues) was confirmed using anti-adhesion assay.

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Hydrogenation Selectivity of the Bicyclo[4.4.0]decane Ring System of Valencanes

Abstract: To test the selectivity of sterically hindered systems, (+)-nootkatone and derivatives were subjected to a wide variety of hydrogenation methodologies. The steric impact of the C-4 methyl substituent seems to be responsible for the inability of the system to adopt the cis-fused structure.

Cited by 2 publications

References 12 publications

Formation of Alkanes and Arenes by Reduction

Formation of Alkanes and Arenes by Reduction

Total Synthesis and Biological Evaluation of Cell Adhesion Inhibitors Peribysin A and B: Structural Revision of Peribysin B

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