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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric total syntheses of immunosuppressive diterpenoids triptobenzenes N and R via a remote Csp3-H
Nanda Kishore Roy1, Ranjit Murmu1, Mintu Munda2
1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, West Bengal, India. alakesh@iiserkol.ac.in.
Abstract:
The total syntheses of the naturally occurring diterpenoids triptobenzenes N (1c) and R (1d) have been accomplished via a late-stage δ-Csp3-H functionalization of an enone intermediate. The highly functionalized dienone intermediate 2 was utilized as a common scaffold for this study. An XRD analysis of compounds 8 and 4 confirmed the stereochemistry of the quaternary centers of the abietane core. Finally, a chemoselective ketal protection and reduction completed the first total syntheses of the immunosuppressive diterpenoids triptobenzenes N (1c) and R (1d).
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