Issue 4, 2015

Synthetic strategies toward the decalin motif of maklamicin and related spirotetronates

Abstract

Herein we describe a scalable approach to the decalin moiety of maklamicin. Key to the synthesis is an intramolecular Diels–Alder (IMDA) reaction that proceeds via an endo-axial transition state to generate the desired stereochemistry. We explored the diastereoselectivity of the IMDA reaction as a function of both chiral catalysis and acyclic precursor stereochemistry.

Graphical abstract: Synthetic strategies toward the decalin motif of maklamicin and related spirotetronates

Supplementary files

Article information

Article type
Research Article
Submitted
16 dec 2014
Accepted
16 feb 2015
First published
16 feb 2015

Org. Chem. Front., 2015,2, 388-393

Author version available

Synthetic strategies toward the decalin motif of maklamicin and related spirotetronates

M. H. Lacoske, J. Xu, N. Mansour, C. Gao and E. A. Theodorakis, Org. Chem. Front., 2015, 2, 388 DOI: 10.1039/C4QO00332B

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