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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.

SUBMITTER: Lacoske MH

PROVIDER: S-EPMC4527581 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Lacoske Michelle H MH Xu Jing J Mansour Noel N Gao Chao C Theodorakis Emmanuel A EA

Organic chemistry frontiers : an international journal of organic chemistry 20150401 4

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 <i>endo</i>-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. ...[more]

PMID: 26257916

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