Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure

K C Nicolaou; Scott A Snyder; Xianhai Huang; Klaus B Simonsen; Alexandros E Koumbis; Antony Bigot

doi:10.1021/ja040090y

Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure

J Am Chem Soc. 2004 Aug 18;126(32):10162-73. doi: 10.1021/ja040090y.

Authors

K C Nicolaou¹, Scott A Snyder, Xianhai Huang, Klaus B Simonsen, Alexandros E Koumbis, Antony Bigot

Affiliation

¹ Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu

PMID: 15303892
DOI: 10.1021/ja040090y

Abstract

A brief introduction into the chemistry of diazonamide A (1) is followed by first-generation sequences to access the originally proposed structure for this unusual marine natural product. These explorations identified a route capable of delivering a model compound possessing the complete heteroaromatic core of the natural product, highlighting in the process several unanticipated synthetic challenges which led both to new methodology as well as an improved synthetic plan that was successfully applied to fully functionalized intermediates.

Publication types

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

MeSH terms

Epidermal Growth Factor / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Heterocyclic Compounds, 4 or More Rings / chemistry*
Indoles / chemistry
Oxazoles / chemical synthesis
Oxazoles / chemistry*
Peptide Fragments / chemistry

Substances

Heterocyclic Compounds, 4 or More Rings
Indoles
Oxazoles
Peptide Fragments
diazonamide A
Epidermal Growth Factor