Synthesis 2017; 49(20): 4711-4716
DOI: 10.1055/s-0036-1589067
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel–Crafts Reaction

Authors

  • Bao Nguyen Do Doan

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore   Email: roderick@ntu.edu.sg
  • Xin Yi Tan

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore   Email: roderick@ntu.edu.sg
  • Chin May Ang

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore   Email: roderick@ntu.edu.sg
  • Roderick W. Bates*

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore   Email: roderick@ntu.edu.sg

We thank the Agency for Science Technology and Research (A-Star) for financial support of this work (PSF grant number 1321202095). B.N.D.D. thanks the URECA programme of NTU for support.
Further Information

Publication History

Received: 29 April 2017

Accepted after revision: 26 May 2017

Publication Date:
20 July 2017 (online)


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Abstract

A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel–Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.

Supporting Information