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Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin.
Org Lett. 2003 May 01; 5(9):1563-5.OL

Abstract

A palladium-catalyzed asymmetric allylic alkylation effects a dynamic kinetic asymmetric transformation of racemic isoprene monoepoxide and a surrogate for Nazarov's reagent in which a quaternary center is created with exellent ee. The resultant adduct allows easy access to a substrate for ring-closing metathesis to form a cyclopentenone and sets the stage for an 11-step synthesis of the cyclopentyl core of the antibiotic antitumor agent viridenomycin. [reaction: see text]

Authors+Show Affiliations

Trost BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Jiang C
No affiliation info available

MeSH

AlkylationAllyl CompoundsAntibiotics, AntineoplasticButadienesCatalysisCyclizationCyclopentanesEpoxy CompoundsHemiterpenesLactamsOrganometallic CompoundsPalladiumPentanesStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12713324

Citation

Trost, Barry M., and Chunhui Jiang. "Pd-catalyzed Asymmetric Allylic Alkylation. a Short Route to the Cyclopentyl Core of Viridenomycin." Organic Letters, vol. 5, no. 9, 2003, pp. 1563-5.
Trost BM, Jiang C. Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin. Org Lett. 2003;5(9):1563-5.
Trost, B. M., & Jiang, C. (2003). Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin. Organic Letters, 5(9), 1563-5.
Trost BM, Jiang C. Pd-catalyzed Asymmetric Allylic Alkylation. a Short Route to the Cyclopentyl Core of Viridenomycin. Org Lett. 2003 May 1;5(9):1563-5. PubMed PMID: 12713324.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin. AU - Trost,Barry M, AU - Jiang,Chunhui, PY - 2003/4/26/pubmed PY - 2003/8/9/medline PY - 2003/4/26/entrez SP - 1563 EP - 5 JF - Organic letters JO - Org Lett VL - 5 IS - 9 N2 - A palladium-catalyzed asymmetric allylic alkylation effects a dynamic kinetic asymmetric transformation of racemic isoprene monoepoxide and a surrogate for Nazarov's reagent in which a quaternary center is created with exellent ee. The resultant adduct allows easy access to a substrate for ring-closing metathesis to form a cyclopentenone and sets the stage for an 11-step synthesis of the cyclopentyl core of the antibiotic antitumor agent viridenomycin. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12713324/Pd_catalyzed_asymmetric_allylic_alkylation__A_short_route_to_the_cyclopentyl_core_of_viridenomycin_ DB - PRIME DP - Unbound Medicine ER -