The Mukaiyama aldol-Prins (MAP) cyclization of acetals stereoselectively provided substituted tetrahydropyrans. The scope of the reaction has been expanded to include other electrophiles, including ketals and α-acetoxy ethers. Finally, a double MAP cyclization with orthoformates is described.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2951841 | PMC |
| http://dx.doi.org/10.1055/s-2008-1032053 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A facile method for the synthesis of highly substituted six-membered rings: Mukaiyama-Aldol-Prins cascade reaction.
Org Lett
June 2010
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
A highly efficient cascade reaction has been developed using cheap commercially available or easily accessible starting materials. It has the ability to construct highly functionalized six-membered ring with three to four stereogenic centers in high yields.
View Article and Find Full Text PDFAssignment of absolute configuration to SCH 351448 via total synthesis.
Org Lett
July 2008
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.
View Article and Find Full Text PDFLewis Acid-Promoted Mukaiyama Aldol-Prins (MAP) Cyclizations of Acetals, Ketals, α-Acetoxy Ethers, and Orthoformates.
Synlett
February 2008
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697.
The Mukaiyama aldol-Prins (MAP) cyclization of acetals stereoselectively provided substituted tetrahydropyrans. The scope of the reaction has been expanded to include other electrophiles, including ketals and α-acetoxy ethers. Finally, a double MAP cyclization with orthoformates is described.
View Article and Find Full Text PDFTotal synthesis of leucascandrolide a: a new application of the Mukaiyama aldol-Prins reaction.
J Org Chem
July 2007
Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, Irvine, CA 92697, USA.
A total synthesis of the marine natural product leucascandrolide A has been completed. The titanium tetrabromide-mediated Mukaiyama aldol-Prins (MAP) reaction with aldehydes developed in our group provided a highly convergent and stereoselective method for assembling the core of the molecule. A new class of MAP reactions with acetals is introduced, and mechanistic considerations for both MAP methods are described.
View Article and Find Full Text PDFTitanium(IV)-promoted Mukaiyama aldol-Prins cyclizations.
Org Lett
August 2003
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
[reaction: see text] A new version of the Mukaiyama aldol-Prins (MAP) cyclization has been developed. Unsaturated enol ethers such as 3 were found to couple with aldehydes in the presence of TiBr(4) to give 4-bromotetrahydropyran products. This cascade reaction sequence leads to the formation of two new carbon-carbon bonds, a ring, and three new stereogenic centers.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!