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Davies SG, Fletcher AM, Roberts PM, et al. (-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment. Org Lett. 2017;19(7):1638-1641doi: 10.1021/acs.orglett.7b00434.
Davies, S. G., Fletcher, A. M., Roberts, P. M., Thomson, J. E., & Zimmer, D. (2017). (-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment. Organic letters, 19(7), 1638-1641. https://doi.org/10.1021/acs.orglett.7b00434
Davies, Stephen G, et al. "(-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment." Organic letters vol. 19,7 (2017): 1638-1641. doi: https://doi.org/10.1021/acs.orglett.7b00434
Davies SG, Fletcher AM, Roberts PM, Thomson JE, Zimmer D. (-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment. Org Lett. 2017 Apr 07;19(7):1638-1641. doi: 10.1021/acs.orglett.7b00434. Epub 2017 Mar 17. PMID: 28306263.
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Org Lett. 2017 Apr 07;19(7):1638-1641. doi: 10.1021/acs.orglett.7b00434. Epub 2017 Mar 17.

(-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment.

Organic letters

Stephen G Davies, Ai M Fletcher, Paul M Roberts, James E Thomson, David Zimmer

Affiliations

  1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.

PMID: 28306263 DOI: 10.1021/acs.orglett.7b00434

Abstract

(-)-Pseudodistomin E has been prepared for the first time, allowing its structure and absolute configuration to be confirmed. The established conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate generated the C(2)-stereocenter, and iodolactonisation of a derivative generated the remaining two stereogenic centers. Ensuing iodide displacement was achieved using a tethering strategy, to introduce the nitrogen atom to C(5). Decarboxylative coupling of a carboxylic acid with a dialkylzinc reagent completed construction of the tridecadienyl chain.

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