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Bioscience, Biotechnology, and Biochemistry Volume 78, 2014 - Issue 1
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Organic Chemistry

Syntheses of all the stereoisomers of butanol type 1,7-seco-2,7′-cyclolignane

Satoshi YamauchiFaculty of Agriculture, Ehime University, Matsuyama, Japan;South Ehime Fisheries Research Center, Ainan, JapanCorrespondence[email protected]
,
Chisato TomiyamaFaculty of Agriculture, Ehime University, Matsuyama, Japan
,
Tuti WukirsariFaculty of Agriculture, Ehime University, Matsuyama, Japan
&
Hisashi NishiwakiFaculty of Agriculture, Ehime University, Matsuyama, Japan
Pages 19-28 | Received 20 Sep 2013, Accepted 16 Oct 2013, Published online: 14 Apr 2014

References

  • Ayres DC, Loike JD. Lignans: chemical, biological and clinical properties. Cambridge: Cambridge University Press; 1990 A registry of the natural lignans; p. 12–84.
  • Ward RS. Lignans, neolignans, and related compounds. Nat. Prod. Rep. 1999;16:75–96.
  • Moss GP. Nomenclature of lignans and neolignans (IUPAC recommendations 2000). Pure Appl. Chem. 2000;72:1493–1523.
  • Xu S, Li N, Ning M-M, Zhou C-H, Yang Q-R, Wang M-W. Bioactive compounds from Peperomia pellucida. J. Nat. Prod. 2006;69:247–250.
  • Wu J-J, Li N, Hasegawa T, Sakai J, Mitsui T, Ogura H, Kataoka T, Oka S, Kiuchi M, Tomida A, Turuo T, Li M, Tang W, Ando M. Bioactive secolignans from Peperomia dindygulensis. J. Nat. Prod. 2006;69:790–794.
  • Zhang G-L, Li N, Wang Y-H, Zheng Y-T, Zhang Z, Wang M-W. Bioactive secolignans from Peperomia heyneana. J. Nat. Prod. 2007;70:662–664.
  • Xu L-J, Huang F, Chen S-B, Li L-N, Chen S-L, Xiao P-G. A cytotoxic neolignan from Schisandra propinqua (Wall.) Baill. J. Integr. Plant Biol. 2006;48:1493–1497.
  • Gao X-M, Pu J-X, Huang S-X, Yang L-M, Huang H, Xiao W-L, Zheng Y-T, Sun H-D. Lignans from Kadsura angustifolia. J. Nat. Prod. 2008;71:558–563.
  • Akiyama K, Yamauchi S, Maruyama M, Sugahara T, Kishida T, Koba Y. Antimicrobial activity of stereoisomers of morinol A and B, tetrahydropyran sesquineolignans. Biosci. Biotechnol. Biochem. 2009;73:129–133.
  • Nakato T, Yamauchi S, Tago R, Akiyama K, Maruyama M, Sugahara T, Kishida T, Koba Y. Syntheses and antimicrobial activity of tetrasusbstituted tetrahydrofuran lignan stereoisomers. Biosci. Biotechnol. Biochem. 2009;73:1608–1617.
  • Kawahara S, Iwata I, Fujita E, Yamawaki M, Nishiwaki H, Sugahara T, Yamauchi S, Akiyama K, Kishida T. IgE-suppressive activity of (-)-matairesinol and its structure-activity relationship. Biosci. Biotechnol. Biochem. 2010;74:1878–1883.
  • Nishiwaki H, Hasebe A, Kawaguchi Y, Akamatsu M, Shuto Y, Yamauchi S. Larvicidal activity of (-)-dihydroguaiaretic acid derivatives against Culex pipiens. Biosci. Biotechnol. Biochem. 2011;75:1735–1739.
  • Nishiwaki H, Kumamoto M, Shuto Y, Yamauchi S. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibition activities. J. Agric. Food Chem. 2011;59:13089–13095.
  • Morita M, Nishiwaki H, Shingai Y, Fujimoto A, Masuda T, Yamauchi S. First diastereoselective construction of butane-type and butyrolactone-type secocyclolignane structures. Biosci. Biotechnol. Biochem. 2011;75:939–943.
  • Yamauchi S, Hayashi Y, Nakashima Y, Kirikihira T, Yamada K, Masuda T. Effect of benzylic oxygen on the antioxidant activity of phenolic lignans. J. Nat. Prod. 2005;68:1459–1470.
  • Stadler D, Bach T. Concise stereoselective synthesis of (-)-podophyllotoxin by an intermolecular iron (III)-catalyzed Friedel-Crafts alkylation. Angew. Chem. Int. Ed. 2008;47:7557–7559.
  • England DB, Kerr MA. Synthesis and cross-coupling reactions of substituted 5-triflyloxyindoles. J. Org. Chem. 2005;70:6519–6522.
  • Rye CE, Barker D. Asymmetric synthesis of (+)-galbelgin, (-)-kadangustin J, (-)-cyclogalgravin and (-)-pycnanthulignenes A and B, three structurally distinct lignan classes, using a common chiral precursor. J. Org. Chem. 2011;76:6636–6648.

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