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Synthesis of the C1-C12 fragment of iriomoteolide 1a by sequential catalytic asymmetric vinylogous aldol reactions.
Org Lett. 2008 Oct 16; 10(20):4645-8.OL

Abstract

An efficient synthesis of the C1-C12 fragment of iriomoteolide 1a has been accomplished via sequential application of two catalytic, asymmetric, vinylogous aldol reactions: a catalytic vinylogous aldol reaction was used to enantioselectively introduce the C5-C8 segment, and a second catalytic vinylogous aldol reaction was used to install the remaining two stereocenters and a stereodefined alkene in the form of an alpha,beta-unsaturated delta-lactone in one step.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fang L
Department of Chemistry, Texas A&M University, College Station, Texas 77842-3092, USA.
Xue H
No affiliation info available
Yang J
No affiliation info available

MeSH

AldehydesCarbonCatalysisMacrolidesMolecular StructureStereoisomerismVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

18811173

Citation

Fang, Lijing, et al. "Synthesis of the C1-C12 Fragment of Iriomoteolide 1a By Sequential Catalytic Asymmetric Vinylogous Aldol Reactions." Organic Letters, vol. 10, no. 20, 2008, pp. 4645-8.
Fang L, Xue H, Yang J. Synthesis of the C1-C12 fragment of iriomoteolide 1a by sequential catalytic asymmetric vinylogous aldol reactions. Org Lett. 2008;10(20):4645-8.
Fang, L., Xue, H., & Yang, J. (2008). Synthesis of the C1-C12 fragment of iriomoteolide 1a by sequential catalytic asymmetric vinylogous aldol reactions. Organic Letters, 10(20), 4645-8. https://doi.org/10.1021/ol801940r
Fang L, Xue H, Yang J. Synthesis of the C1-C12 Fragment of Iriomoteolide 1a By Sequential Catalytic Asymmetric Vinylogous Aldol Reactions. Org Lett. 2008 Oct 16;10(20):4645-8. PubMed PMID: 18811173.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of the C1-C12 fragment of iriomoteolide 1a by sequential catalytic asymmetric vinylogous aldol reactions. AU - Fang,Lijing, AU - Xue,Haoran, AU - Yang,Jiong, Y1 - 2008/09/24/ PY - 2008/9/25/pubmed PY - 2008/12/17/medline PY - 2008/9/25/entrez SP - 4645 EP - 8 JF - Organic letters JO - Org Lett VL - 10 IS - 20 N2 - An efficient synthesis of the C1-C12 fragment of iriomoteolide 1a has been accomplished via sequential application of two catalytic, asymmetric, vinylogous aldol reactions: a catalytic vinylogous aldol reaction was used to enantioselectively introduce the C5-C8 segment, and a second catalytic vinylogous aldol reaction was used to install the remaining two stereocenters and a stereodefined alkene in the form of an alpha,beta-unsaturated delta-lactone in one step. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/18811173/Synthesis_of_the_C1_C12_fragment_of_iriomoteolide_1a_by_sequential_catalytic_asymmetric_vinylogous_aldol_reactions_ L2 - https://doi.org/10.1021/ol801940r DB - PRIME DP - Unbound Medicine ER -