Efficient syntheses of naturally occurring linear dihydronaphthopyran (6a) and its angular analogues (3b and 4), from appropriate ortho-methoxynaphthaldehydes, have been described.
(a) WilsonG., ZenkM. H., InoueK., ShiobaraY., NayeshiroH., and InoueH., Phytochemistry, 1984, 23, 307; (b) H. Itokawa, Y. Qiao and K. H. Takeya, Phytochemistry, 1991, 637; (c) L. Hari, F. DeBuyck and H. DePooter, Phytochemistry, 1991, 1726.
2.
BurnettA.R., and ThomsonR. H., J. Chem. Soc., 1968, 850.
3.
LivingstoneR., and WhitingM. C., J. Chem. Soc., 1955, 3631.
4.
BurnettA.R., and ThomsonR. H., J. Chem. Soc., 1968, 854.
5.
RayS., GroverP. K., KambojV. P., ShettyB. S., and KarA. B., J. Med. Chem., 1976, 276.
6.
BowersW.S., OhtaT., CleereJ. S., and MarsellaP. A., Science, 1976, 193, 542.
7.
(a) BanerjiA., and GoomerN. C., Ind. J. Chem., 1981, 20B, 144 and references cited therein; (b) R. C. Bertelson, Techniques of Chemistry III 1971, 45. Edited by A. Weissberger (Wiley, New York).
8.
RindfuszR.E., GinningsP. M., and HarnackV. L., J. Am. Chem. Soc., 1920, 157.
9.
BellK.H., and DuewellH., Austr. J. Chem., 1963, 16, 690.
10.
CagniantP., and CharauxC., Bull. Soc. Chim. France, 1966, 10, 3249.
11.
AbeywikremaA.N., BeckwithA. L. J., and GerbaS., J. Org. Chem., 1987, 52, 4072.
12.
MiyauraN., IshiyamaT., SasakiH., IshikawaM., SatoM., and SuzukiA., J. Am. Chem. Soc., 1989, 111, 314.
13.
ChowY.L., ZhouX. M., GaitanT. J., and WuZ. Z., J. Am. Chem. Soc., 1989, 111, 3813.
14.
TadaM., HiratsukaM., and GotoH., J. Org. Chem., 1990, 55, 4364.
15.
SugaS., ManabeT., and YoshidaJ., J. Chem. Soc., Chem. Commun., 1999, 13, 1237.
16.
YorimitsuH., ShinokobuH., and OshimaK., Chem. Lett., 2000, 2, 104.
17.
idem, Bull. Chem. Soc. Jpn., 2001, 74, 225.
18.
CliveD.L. J., and WangJ., J. Org. Chem., 2002, 67, 1192.
19.
AnjaneyuluA.S. R., and RaoD. S., Ind. J. Chem. Sect. B., 1997, 36B, 424.
20.
ParadkarM.V., GodboleH. M., RanadeA. A., and JosephA. R., J. Chem. Res. (S), 1998, 318.
21.
NarasimhanN.S., and MaliR. S., Tetrahedron, 1975, 31, 1005.
22.
NarasimhanN.S., and MaliR. S., Tetrahedron. Lett., 1973, 843.
23.
NarasimhanN.S., and AlurkarR. H, Ind. J. Chem., 1969, 621.
24.
DeyD.B., RaoR. H. R., and ShankarnarayananY., J. Ind. Chem. Soc., 1932, 9, 71.
25.
DasguptaA.K., ChatterjeeR. M., and DasK. R., J. Chem. Soc. (C), 1969, 2618.
