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Total synthesis of (+)-crocacin C using hidden symmetry.
J Org Chem. 2010 Mar 05; 75(5):1354-9.JO

Abstract

A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ee >98%).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Candy M
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 CNRS UMR 6263-équipe STeRéO, Campus Saint-Jérôme, 13397 Marseille cedex 20, France.
Audran G
No affiliation info available
Bienaymé H
No affiliation info available
Bressy C
No affiliation info available
Pons JM
No affiliation info available

MeSH

AlkenesAmidesCatalysisCyclizationModels, MolecularMolecular StructureStereoisomerismStructure-Activity Relationship

Pub Type(s)

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

Language

eng

PubMed ID

20128625

Citation

Candy, Mathieu, et al. "Total Synthesis of (+)-crocacin C Using Hidden Symmetry." The Journal of Organic Chemistry, vol. 75, no. 5, 2010, pp. 1354-9.
Candy M, Audran G, Bienaymé H, et al. Total synthesis of (+)-crocacin C using hidden symmetry. J Org Chem. 2010;75(5):1354-9.
Candy, M., Audran, G., Bienaymé, H., Bressy, C., & Pons, J. M. (2010). Total synthesis of (+)-crocacin C using hidden symmetry. The Journal of Organic Chemistry, 75(5), 1354-9. https://doi.org/10.1021/jo902582w
Candy M, et al. Total Synthesis of (+)-crocacin C Using Hidden Symmetry. J Org Chem. 2010 Mar 5;75(5):1354-9. PubMed PMID: 20128625.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (+)-crocacin C using hidden symmetry. AU - Candy,Mathieu, AU - Audran,Gérard, AU - Bienaymé,Hugues, AU - Bressy,Cyril, AU - Pons,Jean-Marc, PY - 2010/2/5/entrez PY - 2010/2/5/pubmed PY - 2010/5/11/medline SP - 1354 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 5 N2 - A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ee >98%). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20128625/Total_synthesis_of__+__crocacin_C_using_hidden_symmetry_ L2 - https://doi.org/10.1021/jo902582w DB - PRIME DP - Unbound Medicine ER -