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The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.
Nat Prod Rep. 2014 Apr; 31(4):563-94.NP

Abstract

The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis and cluster them into the four groups that can be obtained from different silyl ketene acetals or enol ethers. At the beginning, an overview on different stereoselective VMARs is presented; disregarding their applications in total syntheses.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kalesse M
Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany. Markus.Kalesse@oci.uni-hannover.de.
Cordes M
No affiliation info available
Symkenberg G
No affiliation info available
Lu HH
No affiliation info available

MeSH

AldehydesBiological ProductsMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

24595879

Citation

Kalesse, Markus, et al. "The Vinylogous Mukaiyama Aldol Reaction (VMAR) in Natural Product Synthesis." Natural Product Reports, vol. 31, no. 4, 2014, pp. 563-94.
Kalesse M, Cordes M, Symkenberg G, et al. The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis. Nat Prod Rep. 2014;31(4):563-94.
Kalesse, M., Cordes, M., Symkenberg, G., & Lu, H. H. (2014). The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis. Natural Product Reports, 31(4), 563-94. https://doi.org/10.1039/c3np70102f
Kalesse M, et al. The Vinylogous Mukaiyama Aldol Reaction (VMAR) in Natural Product Synthesis. Nat Prod Rep. 2014;31(4):563-94. PubMed PMID: 24595879.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis. AU - Kalesse,Markus, AU - Cordes,Martin, AU - Symkenberg,Gerrit, AU - Lu,Hai-Hua, Y1 - 2014/03/05/ PY - 2014/3/6/entrez PY - 2014/3/7/pubmed PY - 2014/5/28/medline SP - 563 EP - 94 JF - Natural product reports JO - Nat Prod Rep VL - 31 IS - 4 N2 - The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis and cluster them into the four groups that can be obtained from different silyl ketene acetals or enol ethers. At the beginning, an overview on different stereoselective VMARs is presented; disregarding their applications in total syntheses. SN - 1460-4752 UR - https://www.unboundmedicine.com/medline/citation/24595879/The_vinylogous_Mukaiyama_aldol_reaction__VMAR__in_natural_product_synthesis_ DB - PRIME DP - Unbound Medicine ER -