Tags

Type your tag names separated by a space and hit enter

Stereoselective rhodium-catalyzed conjugate addition of boronic acids to unprotected delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and beta-substituted derivatives.
J Org Chem. 2009 Jan 02; 74(1):466-9.JO

Abstract

The chiral delta-hydroxy-gamma-butanolide moiety is widely found among biologically active natural products. We report herein the stereoselective synthesis of beta-substituted analogues of these compounds by the Rh(I)-catalyzed conjugate addition of boronic acids to chiral delta-hydroxy-gamma-butenolides, easily prepared from the chiral pool. The reaction takes place with high trans diastereoselectivity without protection of the hydroxyl group. The three-step syntheses of (-)-7-oxamuricatacin (R1 = H, R2 = CH2-O-(n)C10H21) and of new beta-substituted 7-oxamuricatacin analogues (R1 = aryl, vinyl) is reported.

Authors+Show Affiliations

Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19053603

Citation

Navarro, Cristina, et al. "Stereoselective Rhodium-catalyzed Conjugate Addition of Boronic Acids to Unprotected Delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and Beta-substituted Derivatives." The Journal of Organic Chemistry, vol. 74, no. 1, 2009, pp. 466-9.
Navarro C, Moreno A, Csákÿ AG. Stereoselective rhodium-catalyzed conjugate addition of boronic acids to unprotected delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and beta-substituted derivatives. J Org Chem. 2009;74(1):466-9.
Navarro, C., Moreno, A., & Csákÿ, A. G. (2009). Stereoselective rhodium-catalyzed conjugate addition of boronic acids to unprotected delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and beta-substituted derivatives. The Journal of Organic Chemistry, 74(1), 466-9. https://doi.org/10.1021/jo8022395
Navarro C, Moreno A, Csákÿ AG. Stereoselective Rhodium-catalyzed Conjugate Addition of Boronic Acids to Unprotected Delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and Beta-substituted Derivatives. J Org Chem. 2009 Jan 2;74(1):466-9. PubMed PMID: 19053603.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective rhodium-catalyzed conjugate addition of boronic acids to unprotected delta-hydroxy-gamma-butenolides. Synthesis of (-)-7-oxamuricatacin and beta-substituted derivatives. AU - Navarro,Cristina, AU - Moreno,Ana, AU - Csákÿ,Aurelio G, PY - 2008/12/5/pubmed PY - 2009/2/13/medline PY - 2008/12/5/entrez SP - 466 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 1 N2 - The chiral delta-hydroxy-gamma-butanolide moiety is widely found among biologically active natural products. We report herein the stereoselective synthesis of beta-substituted analogues of these compounds by the Rh(I)-catalyzed conjugate addition of boronic acids to chiral delta-hydroxy-gamma-butenolides, easily prepared from the chiral pool. The reaction takes place with high trans diastereoselectivity without protection of the hydroxyl group. The three-step syntheses of (-)-7-oxamuricatacin (R1 = H, R2 = CH2-O-(n)C10H21) and of new beta-substituted 7-oxamuricatacin analogues (R1 = aryl, vinyl) is reported. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19053603/Stereoselective_rhodium_catalyzed_conjugate_addition_of_boronic_acids_to_unprotected_delta_hydroxy_gamma_butenolides__Synthesis_of_____7_oxamuricatacin_and_beta_substituted_derivatives_ L2 - https://doi.org/10.1021/jo8022395 DB - PRIME DP - Unbound Medicine ER -