Abstract
The first total synthesis of the title compound 1 was accomplished starting from α-cyclocitral and benzyl triphenylphosphonium chloride 3 in seven steps via a strategy of AC→ABC. In the synthesis, t-BuOK/t-BuOH system was utilised for enolisation and the iso-propyl group was introduced in the last step.
References
1.
Ulubelen A.
, and
Topcu G.
, J. Nat. Prod. , 1992 , 55 , 441 .
2.
Chen B.
,
Duan H. Q.
, and
Takaishi Y.
, Phytochemistry , 1999 , 51 , 683 .
3.
Bruning R.
, and
Wagner H.
, Phytochemistry , 1978 , 17 , 1821 .
4.
Zhang C.L.
,
Bie P. Y.
,
Peng X. J.
, and
Pan X. F.
, J. Chin. Chem. Soc. , 2003 , 50 , 429 .
5.
Zhang C.L.
,
Bie P. Y.
,
Peng X. J.
, and
Pan X. F.
, Chem. J. Chinese Universities , 2003 , 24 , 1910 .
6.
Wang X.C.
,
Pan X. F.
, and
Cui Y. X.
Tetrahedron , 1996 , 52 , 10 659.
7.
Gan Y.H.
, and
Pan X. F.
J. Chem. Research (S) , 2000 , 130 .
8.
Ernest W.
,
Adriano A.
, and
Peter B.
J. Org. Chem. , 1965 , 30 , 713 .
9.
Grinenko G.S.
,
Popova E. V.
, and
Maksimov V. I.
, Zh. Org. Khim. , 1971 , 7 , 935 .
10.
Matsumoto T.
, and
Usui S.
, Bull. Chem. Soc. Jpn. , 1979 , 52 , 212 .