Stereoselective construction of tetra-substituted tetrahydrofuran compounds from benzylic hemiacetal in the presence 0of H2 and a Pd catalyst: Stereoselective synthesis of a stereoisomer of (-)-virgatusin and its antimicrobiological activity

Bioscience, Biotechnology and Biochemistry

Volumn 72, Issue 1, 2008, Pages 197-203

  Nakato, Tomofumi ^a   Tago, Ryosuke ^a   Akiyama, Koichi ^a   Maruyama, Masafumi ^a   Sugahara, Takuya ^a   Kishida, Taro ^a   Yamauchi, Satoshi ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Antimicrobiological activity; Tetrahydrofuran lignan; Virgatusin

Indexed keywords

ANTIMICROBIOLOGICAL ACTIVITY; BENZYLIC HEMIACETAL; STEREOSELECTIVE CONVERSION;

MICROBIOLOGY; ORGANIC COMPOUNDS; PALLADIUM; STEREOSELECTIVITY;

CATALYST ACTIVITY;

ANTIINFECTIVE AGENT; BENZYL DERIVATIVE; FURAN DERIVATIVE; POLYACETAL; POLYMER; SOLVENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG; VIRGATUSIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BENZYL COMPOUNDS; CATALYSIS; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OPTICAL ROTATION; POLYMERS; SOLVENTS;

TETRA;

EID: 38749107235     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.70554     Document Type: Article

References (14)

1. Czernecki, S., and Ville, G., C-glycosides 7. Stereospecific C-glycosylation of aromatic and heterocyclic rings. J. Org. Chem., 54, 610-612 (1989).
2. Shing, T. K. M., and Gillhouley, J. G., Enantiospecific synthesis of (+)-altholactone and its three stereoisomers. Tetrahedron, 50, 8685-8698 (1994).
3. Nishiyama, Y., Tujino, T., Yamano, T., Hayashishita, M., and Itoh, K., Stereoselective synthesis of trans-2,5-disubstituted tetrahydrofuran via the Lewis acid mediated reduction of cyclic hemiketals with triphenylsilane. Chem. Lett., 165-166 (1997).
4. Shionoya, M., and Tanaka, K., Synthetic incorporation of metal complexes into nuleic acids and peptides directed toward functionalized molecules. Bull. Chem. Soc. Japan, 73, 1945-1954 (2000).
5. Schmitt, A., and Reißig, H.-U., On the stereoselectivity of γ-lactol substitutions with allyl- and propargylsilanes-synthesis of disubstituted tetrahydrofuran derivatives. Eur. J. Org. Chem., 3893-3901 (2000).
6. Shi, H., Liu, H., Bloch, R., and Mandville, G., A novel efficient and stereoselective synthesis of cis- or trans-2,5-disubstituted tetrahydrofurans. Tetrahedron, 57, 9335-9341 (2001).
7. Yoda, H., Mizutani, M., and Takabe, K., First total synthesis of tetrasubstituted tetrahydrofuran lignan, (-)-virgatusin. Tetrahedron Lett., 40, 4701-4702 (1999).
8. Wilcox, C. S., and Cowart, M. D., New approaches to synthetic receptors. Studies on the synthesis and properties of macrocyclic C-glycosyl compounds as chiral, water-soluble cyclophanes. Carbohydr. Res., 171, 141-160 (1987).
9. Mailoli, A. T., Civiello, R. L., Foxman, B. M., and Gordon, D. M., Asymmetric synthesis of sesaminone: confirmation of its structure and determination of its absolute configuration. J. Org. Chem., 62, 7413-7417 (1997).
10. Yamauchi, S., Okazaki, M., Akiyama, K., Sugahara, T., Kishida, T., and Kashiwagi, T., First enantio-selective synthesis of (-)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan. Org. Biomol. Chem., 3, 1670-1675 (2005).
11. Rao, K. V., and Alvarez, F. M., Chemistry of Saururus cernuus III: some reactions of the diarylbutane-type neolignans. J. Nat. Prod., 48, 592-597 (1985).
12. Yamauchi, S., Nakato, T., Tsuchiya, M., Akiyama, K., Maruyama, M., Sugahara, T., and Kishida, T., Use of benzyl mesylate for the synthesis of tetrahydrofuran lignan: syntheses of 7,8-trans, 7′,8′- trans, 7,7′-cis, and 8,8′-cis-virgatusin stereoisomers. Biosci. Biotechnol. Biochem., 71, 2248-2255 (2007).
13. Maruyama, M., Yamauchi, S., Akiyama, K., Sugahara, T., Kishida, T., and Koba, Y., Antibacterial activity of a virgatusin-related compound. Biosci. Biotechnol. Biochem., 71, 677-680 (2007).
14. Akiyama, K., Yamauchi, S., Nakato, T., Maruyama, M., Sugahara, T., and Kishida, T., Antifungal activity of tetra-substituted tetrahydrofuran lignan, (-)-virgatusin, and its structure-activity relationship. Biosci. Biotechnol. Biochem., 71, 1028-1035 (2007).