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Towards the Total Synthesis of Haplomyrtin

Hunter, Nora Ellen
http://rave.ohiolink.edu/etdc/view?acc_num=wright1277319775

Abstract Details

2010, Master of Science (MS), Wright State University, Chemistry.
Haplomyrtin, a 1-aryl-2,3-naphthalide lignan obtained from Turkish Haplophyllum myrtifolium and Haplophyllum telephioides offers a number of synthetic challenges with the incorporation of two aromatic hydroxyl groups at positions C4 and C7 on the naphthalene ring system and regiospecific condensation of the γ-lactone ring. Improvements towards the total synthesis of haplomyrtin were pursued with commercially available vanillin and piperonal in a total of 8 separate steps. All steps have excellent reproducibility. This strategy includes bromination of protected vanillin to yield 2-(4-(4-methoxybenzyloxy)-2-bromo-5-methoxyphenyl)-1,3-dioxolane and 2-(4-(benzyloxy)-2-bromo-5-methoxyphenyl)-1, 3-dioxolane in 48% and 88% yield respectively, and incorporation of the fully functionalized pendant aryl ring through a lithium-halogen exchange followed by coupling with piperonal. The C4 hydroxyl group is placed by the in-situ formation of an isobenzofuran and subsequent Diels-Alder reaction with DMAD to yield the diester precursor to haplomyrtin, Dimethyl 1-(benzo[d][1,3]dioxol-5-yl)-7-(benzyloxy)-4-hydroxy-6-methoxynaphthalene-2,3-dicarboxylate, in 52% yield.
Willian Feld, PhD (Advisor)
Kenneth Turnbull, PhD (Committee Member)
Eric Fossum, PhD (Committee Chair)
71 p.
Chemistry
Haplomytin; 1-aryl-2,3-naphthalide lignan; Haplophyllum myrtifolium; Haplophyllum telephioides; arylnaphthalene lignan; vanillin; piperonal; DMAD; lithium-halogen exchange; Diels-Alder; annulation; isobenzofuran

Recommended Citations

Citations

  • Hunter, N. E. (2010). Towards the Total Synthesis of Haplomyrtin [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1277319775

    APA Style (7th edition)

  • Hunter, Nora. Towards the Total Synthesis of Haplomyrtin. 2010. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1277319775.

    MLA Style (8th edition)

  • Hunter, Nora. "Towards the Total Synthesis of Haplomyrtin." Master's thesis, Wright State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=wright1277319775

    Chicago Manual of Style (17th edition)

wright1277319775
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© 2010, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.