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Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructures.
Org Lett. 2006 Mar 02; 8(5):891-4.OL

Abstract

Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides alpha-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.

Authors+Show Affiliations

Cho CW
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Krische MJ
No affiliation info available

MeSH

AldehydesAlkynesBryostatinsCatalysisHydrogenationMacrolidesMolecular StructureOxidation-ReductionPyransRhodiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16494467

Citation

Cho, Chang-Woo, and Michael J. Krische. "Enantioselective Reductive Coupling of Alkynes and Alpha-keto Aldehydes Via Rhodium-catalyzed Hydrogenation: an Approach to Bryostatin Substructures." Organic Letters, vol. 8, no. 5, 2006, pp. 891-4.
Cho CW, Krische MJ. Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructures. Org Lett. 2006;8(5):891-4.
Cho, C. W., & Krische, M. J. (2006). Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructures. Organic Letters, 8(5), 891-4.
Cho CW, Krische MJ. Enantioselective Reductive Coupling of Alkynes and Alpha-keto Aldehydes Via Rhodium-catalyzed Hydrogenation: an Approach to Bryostatin Substructures. Org Lett. 2006 Mar 2;8(5):891-4. PubMed PMID: 16494467.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructures. AU - Cho,Chang-Woo, AU - Krische,Michael J, PY - 2006/2/24/pubmed PY - 2006/12/9/medline PY - 2006/2/24/entrez SP - 891 EP - 4 JF - Organic letters JO - Org Lett VL - 8 IS - 5 N2 - Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides alpha-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16494467/Enantioselective_reductive_coupling_of_alkynes_and_alpha_keto_aldehydes_via_rhodium_catalyzed_hydrogenation:_an_approach_to_bryostatin_substructures_ DB - PRIME DP - Unbound Medicine ER -
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