Abstract
Thionin-sensitised intrazeolite photo-oxygenation of (R)-(-)-α-phellandrene affords (1S,5R)-5-(1-methylethyl)-2-methylidene-3-cyclohexen-1-yl hydroperoxide as the major ene product. This can be easily reduced with triphenylphosphine to the natural product trans-yabunikkeol.
Keywords
References
1.
Ramamurthy V.
,
Lakshminarasimhan P.
,
Grey C.P.
and
Johnston L.J.
, J. Chem. Soc., Chem. Commun. , 1998 , 2411 .
2.
(a)
Li X.
and
Ramamurthy V.
, J. Am. Chem. Soc. , 1996 , 118 , 10666 ;
3.
Stratakis M.
and
Froudakis G.
, Org. Lett. , 2000 , 2 , 1369 ;
4.
(c)
Clennan E.L.
and
Sram J.P.
, Tetrahedron , 2000 , 56 , 6945 .
5.
Stratakis M.
and
Kosmas G.
, Tetrahedron Lett. , 2001 , 42 , 6007 .
6.
Stratakis M.
and
Rabalakos C.
, Tetrahedron Lett. , 2001 , 42 , 4175 .
7.
Atkins R.
and
Carless H.A.J.
, Tetrahedron Lett. , 1987 , 28 , 6093 .
8.
(a)
Matusch R.
and
Schmidt G.
, Angew. Chem., Int. Ed. Engl. , 1988 , 27 , 717 ;
9.
Matusch R.
and
Schmidt G.
, Helv. Chim. Acta , 1989 , 72 , 51 .
10.
Stratakis M.
and
Orfanopoulos M.
, Tetrahedron , 2000 , 56 , 1595 .
11.
Fujita Y.
,
Fujita S.
and
Yoshikawa H.
, Bull. Chem. Soc. Jpn. , 1970 , 43 , 1599 .
12.
Debrauwere J.
and
Verzele M.
, Bull. Soc. Chim. Belg. , 1975 , 84 , 167 .