Abstract
A formal total synthesis of Cacalol is described. Synthesis of methyl tetralin 8 has been achieved from the 5–methoxy-1-tetralone 2. The conversion of 8 into tetralol 11 has been accomplished in three steps (bromination, formylation and oxidation).
References
1.
Romo J.
, and
Joseph-Nathan P.
Tetrahedron , 1964 , 20 , 2331
2.
Kakisawa H.
,
Inouye Y.
, and
Romo J.
Tetrahedron Lett. , 1969 , 10 , 1929
3.
Brown P.M.
, and
Thomson R.H.
J. Chem. Soc. C , 1969 , 1184
4.
Ruiz R.
,
Correa J.
, and
Maldonado L.A.
Bull. Soc. Chim. Fr. , 1969 , 3612
5.
Inman W.D.
,
Luo J.
,
Jolad S.D.
,
King S.R.
, and
Cooper R.
J. Nat. Prod. , 1999 , 62 , 1088
6.
Garduño-Ramírez M.L.
,
Trejo A.
,
Navarro V.
,
Bye R.
,
Linares E.
, and
Delgado G.
J. Nat. Prod. , 2001 , 64 , 432
7.
Poon Ng Po S.
, and
Banerjee A.K.
Nat. Prod. Res. , 2006 , 20 , 629
8.
Inouye Y.
,
Uchida Y.
, and
Kakisawa H.
Chem. Lett. , 1975 , 1317
9.
Yuste F.
, and
Walls F.
Aust. J. Chem. , 1976 , 29 , 2333
10.
Huffman J.W.
, and
Pandian R.
J. Org. Chem. , 1979 , 44 , 1851
11.
Garofalo A.W.
,
Litvak J.
,
Wang L.
,
Dubenko L.G.
,
Cooper R.
, and
Bierer D.E.
J. Org. Chem. , 1999 , 64 , 3369
12.
Part of this work was presented (A.K.B.) at the Sixth Balticum Organicum Syntheticum, Talinn, Estonia, June 25–29, 2006
13.
Howell F.H.
, and
Taylor D.A.H.
J. Chem. Soc. , 1958 , 1248
14.
Harrowven D.C.
, and
Dainty R.F.
, Tetrahedron , 1997 , 53 , 15771
15.
Krishna Mohan K.V.V.
,
Narender N.
,
Srinivasu P.
,
Kulkarni S.J.
, and
Raghavan K.V.
Synth. Commun. , 2004 , 34 , 2143
16.
Jones T.H.
,
Blue M.S.
, and
Fales H.M.
Synth. Commun. , 1981 , 11 , 889
17.
Matsumoto M.
,
Kobayashi H.
, and
Hotta Y.
J. Org. Chem. , 1984 , 49 , 4740 .
