Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones.

Description

No / The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene¿phenol natural
products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation
of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. / EPSRC

Links & Downloads

1. Pritchard, R. G., Sheldrake, H. M., Taylor, I. Z. and Wallace, T. W. (2008). Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones. Tetrahedron Letters, Vol. 49, pp. 4156-4159.
2. http://hdl.handle.net/10454/4665
3. https://doi.org/10.1016/j.tetlet.2008.04.114

Tags

Natural products

Sesquiterpene¿phenol

Merosesquiterpene

Benzo[a]xanthene

Puupehenone

Radical cyclisation

6-endo-Trig

Additional Fields

Identifer	oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/4665
Date	23 June 2008
Creators	Pritchard, R.P., Sheldrake, Helen M., Taylor, I.Z., Wallace, T.W.
Source Sets	Bradford Scholars
Language	English
Detected Language	English
Type	Article, No full-text in the repository