Synthesis 2019; 51(22): 4231-4238
DOI: 10.1055/s-0039-1690180
paper
© Georg Thieme Verlag Stuttgart · New York

Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing an Intermediate for Squalestatin Synthesis

Hasanain A. A. Almohseni
,
Younes Fegheh-Hassanpour
,
Tanzeel Arif
,
David M. Hodgson
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK   Email: david.hodgson@chem.ox.ac.uk
› Author Affiliations
We thank the Higher Committee for Education Development in Iraq, the EPSRC and the Higher Education Commission of Pakistan for studentship support (to H.A.A.A., Y.F.H. and T.A., respectively).
Further Information

Publication History

Received: 08 July 2019

Accepted after revision: 26 July 2019

Publication Date:
13 September 2019 (eFirst)

Abstract

Studies on both the propensity for intramolecular cycloaddition between diazo and alkene functionality, and the tolerance of α-substituted α-diazoesters towards ozone in the presence of an alkene, led to chemoselective alkene ozonolysis of an ε-unsaturated-α-diazoester to give a key racemic diazoketone for the synthesis of 6,7-dideoxysqualestatin H5.

Supporting Information

 
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