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

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
› Author Affiliations
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)


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