Synthesis of the C1-C18 fragment of rhizopodin: late-state introduction of the oxazole

Tobias Bender; Darran Loits; Jonathan M White; Mark A Rizzacasa

doi:10.1021/ol500261n

Synthesis of the C1-C18 fragment of rhizopodin: late-state introduction of the oxazole

Org Lett. 2014 Mar 7;16(5):1450-3. doi: 10.1021/ol500261n. Epub 2014 Feb 13.

Authors

Tobias Bender¹, Darran Loits, Jonathan M White, Mark A Rizzacasa

Affiliation

¹ School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne , Victoria 3010, Australia.

PMID: 24524264
DOI: 10.1021/ol500261n

Abstract

The synthesis of the C1-C18 fragment of the myxobacteria metabolite rhizopodin is described. Initial attempts at installing the E,E-diene via cross coupling with an oxazole fragment gave poor results. An alternative approach, in which the diene was formed prior and the oxazole introduced by an acylation/O,N-shift protocol, gave the C1-C18 fragment 2 of rhizopodin (1).

Publication types

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

MeSH terms

Macrolides / chemical synthesis
Molecular Structure
Myxococcales / chemistry
Oxazoles / chemical synthesis
Oxazoles / chemistry*
Stereoisomerism

Substances

Macrolides
Oxazoles
rhizopodin