Gold-catalyzed one-step construction of 2,3-dihydro-1H-Pyrrolizines with an electron-withdrawing group in the 5-position: a formal synthesis of 7-methoxymitosene

Ze-Yi Yan; Yuanjing Xiao; Liming Zhang

doi:10.1002/anie.201203678

Gold-catalyzed one-step construction of 2,3-dihydro-1H-Pyrrolizines with an electron-withdrawing group in the 5-position: a formal synthesis of 7-methoxymitosene

Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8624-7. doi: 10.1002/anie.201203678. Epub 2012 Jul 29.

Authors

Ze-Yi Yan¹, Yuanjing Xiao, Liming Zhang

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA.

PMID: 22847823
DOI: 10.1002/anie.201203678

Abstract

What a ring formation! Bicyclic dihydropyrrolizines with an electron-withdrawing group (EWG) at the 5-position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically-controlled regioselectivity, and the generation of destabilized 1-azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7-methoxymitosene.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Catalysis
Chemistry, Pharmaceutical
Gold / chemistry*
Mitomycins / chemical synthesis*
Mitomycins / chemistry
Molecular Structure
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Stereoisomerism

Substances

Anti-Bacterial Agents
Mitomycins
Pyrroles
Gold