A practical method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8, is described. We prepared the natural labdane-type diterpene 5via key intermediate peroxide 9 and coronarin C 1, compound 8 and zerumin B 6via a furan photosensitised oxygenation reactions.
ItokawaH., MoritaH., Planta Med., 1988, 54, 117; K. Dimas, C. Demetzos, M. Marsellos, R. Sotiriadou, M. Malamas and D. Kokkinopoulos, (1998). Planta Med., 64, 208.
3.
ItokawaH., MoritaH., KatouT., TakeyaK., CavalheiroA.J., de OliveiraR.C.B., IshigeM., and MotidomeM., Planta Med., 1988, 54, 311.
4.
MatsudaH., MorikawaT., SakamotoY., ToguchidaI., and YoshikawaM., Heterocycles, 2002, 56, 45; T. Morikawa, H. Matsuda, Y. Sakamoto, K. Ueda, I. Toguchida and M. Yoshikawa Chem. Pharm. Bull., 2002, 50, 1045.
5.
XuH.-X, DongH., and SimK.-Y, Phytochemistry, 1996, 42, 149.
6.
AbasF., LajisN.H., ShaariK., IsrafD.A., StanslasJ., YusufU.K., and RaofS.M., J. Nat. Prod., 2005, 68, 1090.
7.
ZderoC., BohlmannF., and KingR.M., Phytochemistry, 1992, 31, 1631.
8.
(a) SãoE., RibeiroA., AlvesT.M.A., RomahnaA.J., FilhoJ.D. de S., CordellG., and ZaniC.L., Phytochemistry, 2003, 64, 1125; (b) M.C. de la Torre, I. Garãa and M.A. Sierra, J. Nat. Prod., 2002, 65, 661.
9.
JungM., KoI., and LeeS.J. Nat. Prod., 1998, 61, 1394; M. Jung, I. Ko, S. Lee, S.J. Choi, B.H. Youn and S.K. Kim, Bio. Med. Chem. Lett., 1988, 8, 3295; M. Müller; J. Schröder; Ch. Magg and K. Seifert, Tetrahedron Lett., 1998, 39, 4655.
10.
BoukouvalasJ., WangJ-X, MarionO, and NdziB., J. Org. Chem., 2006, 71, 6670.
11.
NakanoT., MartinA., and RojasA., Tetrahedron, 1982, 38, 1217.
12.
VillamizarJ., FuentesJ., SalazarF., TropperE., and AlonsoR., J. Nat. Prod., 2003, 66, 1623 and refs ãted therein; J. Villamizar, F. Salazar, J. Fuentes, E. Tropper and R. Alonso, J. Chem. Res., 2002, 504 and refs ãted therein.
13.
LeyS.V., NormanJ., GriffithW., and MarsdenS., Synthesis, 1994, 639.
14.
FétizonM., GolfierM., and LouisJ-M., Tetrahedron, 1969, 31, 171.
15.
KernanM.R., and FaulknerD.J., J. Org. Chem., 1988, 53, 2773; B.L. Feringa, Recl. Trav. Chim. Pays-Bas, 1987, 106, 469.
16.
TurnerJ.A., and HerzW., J. Org. Chem., 1977, 42, 1900; P.M. Giang, P.T. Son and Otsuka H., Nat. Med., 2004, 58, 230.