Chemical Communications 2011-07-21

Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone.

William P Unsworth, Kiri Stevens, Scott G Lamont, Jeremy Robertson

Index: Chem. Commun. (Camb.) 47(27) , 7659-61, (2011)

Full Text: HTML

Abstract

We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.

Related Compounds

Related Articles:

Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensin.

2008-01-04

[J. Org. Chem. 73(1) , 2-11, (2008)]

The cytotoxicity of naturally occurring styryl lactones.

2006-02-01

[Phytomedicine 13(3) , 181-6, (2006)]

Asymmetric synthesis of (+)-altholactone: a styryllactone isolated from various Goniothalamus species.

2008-01-01

[Chemistry 14(9) , 2842-9, (2008)]

A convergent Pd-catalyzed asymmetric allylic alkylation of dl- and meso-divinylethylene carbonate: enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone.

2007-01-01

[Chemistry 13(34) , 9547-60, (2007)]

Altholactone induces apoptotic cell death in human colorectal cancer cells.

2012-06-01

[Phytother Res. 26(6) , 926-31, (2012)]

More Articles...