Issue 22, 2014

An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence

Abstract

A new asymmetric total synthesis of a phenanthroindolizidine alkaloid (S)-tylophorine is reported, which features a catalytic asymmetric allylation of aldehydes and an unexpected one-pot DMAP promoted isocyanate formation and Lewis acid catalyzed intramolecular cyclization reaction. In addition, White's direct C–H oxidation catalyst system converting monosubstituted olefins to linear allylic acetates was also employed for late-stage transformation.

Graphical abstract: An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence

Supplementary files

Article information

Article type
Paper
Submitted
25 Jan 2014
Accepted
26 Mar 2014
First published
26 Mar 2014

Org. Biomol. Chem., 2014,12, 3616-3621

Author version available

An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence

B. Su, H. Zhang, M. Deng and Q. Wang, Org. Biomol. Chem., 2014, 12, 3616 DOI: 10.1039/C4OB00200H

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