Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives

Compounds that comprise the erythrina alkaloid class of natural products are based on a tetracyclic spiroamine framework and exhibit a range of biological activities on the central nervous system. Herein, we report a new and efficient total synthesis of this multiple‐ring system based on an intramol...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2015-09, Vol.21 (40), p.13909-13912
Main Authors: Monaco, Alessandra, Aliev, Abil E., Hilton, Stephen T.
Format: Article
Language:English
Subjects:
acylal
Alkaloids
Central nervous system
Chemistry
Derivatives
erythrina alkaloids
intramolecular acylal cyclisation
Lewis acid
Libraries
Natural products
Regioselectivity
Strategy
Synthesis
tandem cyclisation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Compounds that comprise the erythrina alkaloid class of natural products are based on a tetracyclic spiroamine framework and exhibit a range of biological activities on the central nervous system. Herein, we report a new and efficient total synthesis of this multiple‐ring system based on an intramolecular acylal cyclisation (IAC) approach. Using this methodology, the tetracyclic core was rapidly assembled over a two‐step domino process catalysed by a Lewis acid. The effect of heteroatoms, substituents and ring size on the IAC has also been investigated, and the broad application of this procedure is demonstrated by the synthesis of a library of derivatives in good yields with excellent regioselectivity. Extending the diversity of the erythrina core: The tetracyclic core of the erythrina alkaloid family can be accessed through a Lewis acid mediated intramolecular acylal cyclisation (IAC) approach in two steps. Using this, heteroatoms and variation of the cyclohexyl ring produced a library of derivatives in good yields and with excellent regioselectivity.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502436