Synthesis of Dihydrobenzo[h]coumarins and Their 4‐Methyl Analogs

References

• Huang , L. , Kashiwada , Y. , Cosentino , L. M. , Fan , S. , Chen , C. H. , McPhail , A. T. , Fujioka , T. , Mihashi , K. and Lee , K. H. 1994 . Anti‐AIDS agents. 15. Synthesis and anti‐HIV activity of dihydroseselins and related analogs . J. Med. Chem. , 37 : 3947
   PubMed Web of Science ®Google Scholar
• Xie , L. , Takeuchi , Y. , Cosentino , L. M. and Lee , K. H. 1999 . Anti‐AIDS agents. 37. Synthesis and structure–activity relationships of (3′R, 4′R)‐(+)‐cis‐khellacto ne‐(+)‐cis‐khellactone derivatives as novel potent anti‐HIV agents . J Med. Chem. , 42 : 2662 – 2672 .
   PubMed Web of Science ®Google Scholar
• Xie , L. , Yu , D. , Wild , C. , Allaway , G. , Turpin , J. , Smith , P. C. and Lee , K. H. 2004 . Anti‐AIDS agents. 52. Synthesis and anti‐HIV activity of hydroxymethyl 3′R, 4′R)‐3′, 4′ ‐di‐O‐(S)‐camphanoyl‐(+)‐cis‐khellactone derivatives . J. Med. Chem. , 47 : 756 – 760 .
   PubMed Web of Science ®Google Scholar
• Chen , Y. , Zhang , Q. , Zhang , B. N. , Xia , P. , Xia , Y. , Yang , Z. Y. , Kilgore , N. , Wild , C. , Morris‐Natschke , S. L. and Lee , K. H. 2004 . Anti‐AIDS agents. 56. Synthesis and anti‐HIV activity of 7‐thia‐di‐O‐(−)‐camphanoyl‐(+)‐cis‐ khellactone (7‐thia‐DCK) analogs . Bioorg. Med. Chem. , 12 : 6383 – 6387 .
   PubMed Web of Science ®Google Scholar
• Xia , P. , Yin , Z. J. , Chen , Y. , Zhang , Q. , Zhang , B. N. , Xia , Y. , Yang , Z. Y. , Kilgore , N. , Wild , C. , Morris‐Natschke , S. L. and Lee , K. H. 2004 . Anti‐AIDS agents. Part 58. Synthesis and anti‐HIV activity of 1‐thia‐di‐O‐(−)‐camphanoyl‐(+)‐cis‐khellactone (1‐thia‐DCK) analogues . Bioorg. Med. Chem. Let. , 14 : 3341 – 3343 .
   PubMed Web of Science ®Google Scholar
• Zhang , Q. , Chen , Y. , Xia , P. , Xia , Y. , Yang , Z. Y. , Yu , D. L. , Morris‐Natschke , S. L. and Lee , K. H. 2004 . Anti‐AIDS agents. Part 62. Anti‐HIV activity of 2‐substituted 4‐methyl‐3′, 4′ di‐O‐(−)‐camphanoyl‐(+)‐cis‐khellactone (4‐methyl DCK) analogs . Bioorg. Med. Chem.Lett. , 14 : 5855 – 5857 .
   PubMed Web of Science ®Google Scholar
• Yu , D. L. , Suzuki , M. , Xie , L. , Morris‐Natsclilce , S. L. and Lee , K. H. 2003 . Recent progress in the development of coumarin derivatives as potent anti‐HIV agents . Med. Res. Rev. , 23 : 322 – 345 .
   PubMed Web of Science ®Google Scholar
• Lee , T. T. , Kashiwada , Y. , Huang , L. , Snider , J. , Cosentino , M. and Lee , K. H. 1994 . Suksdorfin: An anti‐HIV principle from lomatium suksdorfii, its structure–activity correlation with related coumarins, and synergistic effects with anti‐AIDS nucleosides . Bioorg. Med.Chem. , 2 : 1051 – 1056 .
   PubMedGoogle Scholar
• Abd El‐Razek , M. H. , Ohta , S. and Hirata , T. 2003 . Terpenoid coumarins of the genus Ferula . Heterocycles , 60 ( 3 ) : 689 – 716 .
   Web of Science ®Google Scholar
• David , G. C. and Peter , H. H. 1963 . ar‐Tetrahydro‐α‐naphthol (1‐naphthol, 5,6,7,8‐tetrahydro‐) . Org. Synth. Coll. Vol IV , : 887 – 889 .
   Google Scholar
• Wang , Y. , Lu , M. Y. and Xia , P. 2003 . Study on the synthesis of 4‐methyl‐7,10‐dihydrobenzo[h]coumarin . Chin. J. Org. Chem. , 23 : 1396 – 1399 .
   Web of Science ®Google Scholar
• Sriraghavan , K. and Ramakrishnan , V. T. 2001 . A facile synthesis of N‐aryl aziridines synth . Commun. , 31 : 1105 – 1121 .
   Google Scholar
• Chinnaali , K. , Fun , H. K. , Sriraghavan , K. and Ramakrishnan , V. T. 1998 . 4‐Methyl‐7,10‐dihydrobenzo [h]coumarin and 4‐methyl‐7,8,9,10‐tetrahydro‐8,9‐epoxybenzo[h]coumarin . Acta Crystallogr., Sect. , 54 ( 4 ) : 542 – 544 .
   Google Scholar
• Casiraghi , G. , Casnati , G. , Puglia , G. , Sartori , G. and Terenghi , G. 1980 . Selective reactions between phenols and formaldehyde. A novel route to salicylaldehydes . J. Chem. Soc., Perkin Trans. , : 1862 – 1865 .
   Google Scholar
• Eastham , J. F. and Larkin , D. R. 1958 . The base‐catalyzed isomerization of 5,8‐dihydro‐l‐naphthol and its methyl ether . J. Am. Chem. Soc. , 80 : 2887 – 2893 .
   Web of Science ®Google Scholar
• Tsukinoki , T. , Kanda , T. , Liu , G. B. , Tsuzuki , H. and Tashiro , M. 2000 . Organic reaction in water. Part 3: A facile method for reduction of aromatic rings using a Raney Ni–Al alloy in dilute aqueous alkaline solution under mild conditions . Tetrahedron Lett. , 41 : 5865 – 5868 .
   Web of Science ®Google Scholar
• Nakabayashi , T. 1957 . Coumarin derivatives. XI. Catalytic hydrogenation of α‐naphthocoumarin and 4‐methyl‐α‐naphthocoumarin . Yakugaku Zasshi , 77 : 523 – 526 . See also Chem. Abstr. 1957 , 14708a.
   Google Scholar
• Rangarajan , R. and Eisenbraun , E. J. 1985 . Chromic acid oxidation of indans and tetralins to 1‐indanones and 1‐tetralones using Jones and other chromium(VI) reagents . J. Org. Chem. , 50 : 2435 – 2438 .
   Web of Science ®Google Scholar
• Wayland , B. B. , Ba , S. and Sherry , A. E. 1991 . Activation of methane and toluene by rhodium(II) porphyrin complexes . J. Am. Chem. Soc. , 113 : 5305 – 5311 .
   Web of Science ®Google Scholar
• Noureldin , N. A. , Zhao , D. Y. and Lee , D. G. 1997 . Heterogeneous permanganate oxidations. 7. The oxidation of aliphatic side chains . J. Org. chem. , 62 : 8767 – 8772 .
   Web of Science ®Google Scholar
• Dieter , R. K. , Lin , Y. J. and Dieter , J. W. 1984 . 1,3‐Carbonyl transposition methodology employing alpha‐oxo ketene dithioacetals: Application in the synthesis of phenols and (+)‐myodesmone . J. Org. chem. , 49 : 3183 – 3195 .
   Web of Science ®Google Scholar