Synthesis of the griseusin B framework via a one-pot annulation-methylation-double deprotection-spirocyclization sequence

Briar J Naysmith; Margaret A Brimble

doi:10.1021/ol400686f

Synthesis of the griseusin B framework via a one-pot annulation-methylation-double deprotection-spirocyclization sequence

Org Lett. 2013 Apr 19;15(8):2006-9. doi: 10.1021/ol400686f. Epub 2013 Apr 5.

Authors

Briar J Naysmith¹, Margaret A Brimble

Affiliation

¹ School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.

PMID: 23560611
DOI: 10.1021/ol400686f

Abstract

A highly convergent synthesis of the griseusin B scaffold is described. The key step involves an efficient one-pot Hauser-Kraus annulation-methylation-double deprotection-spirocyclization sequence that directly affords the target parent tetracyclic ring system.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biological Products / chemical synthesis*
Biological Products / chemistry
Cyclization
Methylation
Molecular Structure
Naphthoquinones / chemical synthesis
Naphthoquinones / chemistry
Spiro Compounds / chemistry*

Substances

Biological Products
Naphthoquinones
Spiro Compounds
griseusin