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A concise, biomimetic total synthesis of (+)-davanone.
Org Lett. 2009 May 21; 11(10):2217-8.OL

Abstract

A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Morrison KC
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, USA.
Litz JP
No affiliation info available
Scherpelz KP
No affiliation info available
Dossa PD
No affiliation info available
Vosburg DA
No affiliation info available

MeSH

Antifungal AgentsArtemisiaBiological ProductsCatalysisCyclizationEsterificationMolecular StructureOxidation-ReductionPalladiumParasympatholyticsSesquiterpenesStereoisomerismThiazoles

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

19366191

Citation

Morrison, Karen C., et al. "A Concise, Biomimetic Total Synthesis of (+)-davanone." Organic Letters, vol. 11, no. 10, 2009, pp. 2217-8.
Morrison KC, Litz JP, Scherpelz KP, et al. A concise, biomimetic total synthesis of (+)-davanone. Org Lett. 2009;11(10):2217-8.
Morrison, K. C., Litz, J. P., Scherpelz, K. P., Dossa, P. D., & Vosburg, D. A. (2009). A concise, biomimetic total synthesis of (+)-davanone. Organic Letters, 11(10), 2217-8. https://doi.org/10.1021/ol900697w
Morrison KC, et al. A Concise, Biomimetic Total Synthesis of (+)-davanone. Org Lett. 2009 May 21;11(10):2217-8. PubMed PMID: 19366191.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A concise, biomimetic total synthesis of (+)-davanone. AU - Morrison,Karen C, AU - Litz,Jonathan P, AU - Scherpelz,Kathryn P, AU - Dossa,Paul D, AU - Vosburg,David A, PY - 2009/4/16/entrez PY - 2009/4/16/pubmed PY - 2009/6/12/medline SP - 2217 EP - 8 JF - Organic letters JO - Org Lett VL - 11 IS - 10 N2 - A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19366191/A_concise_biomimetic_total_synthesis_of__+__davanone_ L2 - https://doi.org/10.1021/ol900697w DB - PRIME DP - Unbound Medicine ER -