Revised structures are proposed for pseudopterosin G-J aglycon and helioporin E.
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Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.
Angew Chem Int Ed Engl
May 2020
Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
To show the synthetic utility of the catalytic C-C activation of less strained substrates, described here are the collective and concise syntheses of the natural products (-)-microthecaline A, (-)-leubehanol, (+)-pseudopteroxazole, (+)-seco-pseudopteroxazole, pseudopterosin A-F and G-J aglycones, and (+)-heritonin. The key step in these syntheses involve a Rh-catalyzed C-C/C-H activation cascade of 3-arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C-H amination of the tetralone substrate in the synthesis of (-)-microthecaline A, 2) the use of phosphoric acid to enhance efficiency and regioselectivity for problematic cyclopentanone substrates in the C-C activation reactions, and 3) the direct conversion of serrulatane into amphilectane diterpenes by an allylic cyclodehydrogenation coupling.
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Department of Chemistry and Biochemistry , 100 West 18th Avenue , The Ohio State University, Columbus , Ohio 43210 , United States.
A stereogenic center, placed at an exocyclic location next to a chiral carbon in a ring to which it is attached, is a ubiquitous structural motif seen in many bioactive natural products, including di- and triterpenes and steroids. Installation of these centers has been a long-standing problem in organic chemistry. Few classes of compounds illustrate this problem better than serrulatanes and amphilectanes, which carry multiple methyl-bearing exocyclic chiral centers.
View Article and Find Full Text PDFSyntheses and stereochemical revision of pseudopterosin G-J aglycon and helioporin E.
Org Lett
July 2000
Department of Chemistry and Chemical Biology Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Revised structures are proposed for pseudopterosin G-J aglycon and helioporin E.
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