A synthesis of the diazonamide heteroaromatic biaryl macrocycle/hemiaminal core

Matthew A Zajac; Edwin Vedejs

doi:10.1021/ol036179a

A synthesis of the diazonamide heteroaromatic biaryl macrocycle/hemiaminal core

Org Lett. 2004 Jan 22;6(2):237-40. doi: 10.1021/ol036179a.

Authors

Matthew A Zajac¹, Edwin Vedejs

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

PMID: 14723537
DOI: 10.1021/ol036179a

Abstract

[reaction: see text] Stille coupling of an arylstannane aminal 19 with the palladium complex 23 leads to atropisomeric esters 28 and 29. Conversion to macrocycle 30 is demonstrated, a potential precursor of natural and unnatural diazonamides.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Molecular Structure
Oxazoles / chemical synthesis*
Palladium / chemistry

Substances

Heterocyclic Compounds, 4 or More Rings
Oxazoles
diazonamide A
Palladium

Grants and funding

CA17918/CA/NCI NIH HHS/United States