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Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry.
Org Lett. 2013 Feb 15; 15(4):886-9.OL

Abstract

An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently in the synthesis of the C1-C15 and C16-C25 subunits, respectively.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lisboa MP
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, United States.
Jones DM
No affiliation info available
Dudley GB
No affiliation info available

MeSH

AldehydesBiological ProductsMacrolidesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23373594

Citation

Lisboa, Marilda P., et al. "Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and Syn-selective Vinylogous Aldol Chemistry." Organic Letters, vol. 15, no. 4, 2013, pp. 886-9.
Lisboa MP, Jones DM, Dudley GB. Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry. Org Lett. 2013;15(4):886-9.
Lisboa, M. P., Jones, D. M., & Dudley, G. B. (2013). Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry. Organic Letters, 15(4), 886-9. https://doi.org/10.1021/ol400014e
Lisboa MP, Jones DM, Dudley GB. Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and Syn-selective Vinylogous Aldol Chemistry. Org Lett. 2013 Feb 15;15(4):886-9. PubMed PMID: 23373594.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry. AU - Lisboa,Marilda P, AU - Jones,David M, AU - Dudley,Gregory B, Y1 - 2013/02/01/ PY - 2013/2/5/entrez PY - 2013/2/5/pubmed PY - 2013/6/26/medline SP - 886 EP - 9 JF - Organic letters JO - Org Lett VL - 15 IS - 4 N2 - An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently in the synthesis of the C1-C15 and C16-C25 subunits, respectively. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23373594/Formal_synthesis_of_palmerolide_A_featuring_alkynogenic_fragmentation_and_syn_selective_vinylogous_aldol_chemistry_ L2 - https://doi.org/10.1021/ol400014e DB - PRIME DP - Unbound Medicine ER -