Abstract
The total synthesis of lembehyne B was accomplished in five steps in 51% total yield. The cross-cyclomagnesiation of two allenic components, nonadeca-1,2-diene and pentadeca-13,14-dien-1-ol tetrahydropyranyl ether, with EtMgBr in the presence of Mg and Cp2TiCl2 catalyst (10 mol%) was used in the key step of the synthesis.
References
1.
Aoki S., Matsui K., Tanaka K., Satari R., Kobayashi M.
Tetrahedron,
2000
2.
Murakami N., Nakajima T., Kobayashi M.
Tetrahedron Letters,
2001
3.
Zhou Z., Menna M., Cai Y., Guo Y.
Chemical Reviews,
2014
4.
Gung B.W.
Comptes Rendus Chimie,
2008
5.
Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis
Christensen L.P., Brandt K.
Journal of Pharmaceutical and Biomedical Analysis,
2006
6.
Listunov D., Maraval V., Chauvin R., Génisson Y.
Natural Product Reports,
2015
7.
Minto R.E., Blacklock B.J.
Progress in Lipid Research,
2008
8.
Aoki S., Matsui K., Wei H., Murakami N., Kobayashi M.
Tetrahedron,
2002
9.
El Arfaoui D., Listunov D., Fabing I., Oukessou M., Frongia C., Lobjois V., Samson A., Ausseil F., Ben-Tama A., El Hadrami E.M., Chauvin R., Génisson Y.
ChemMedChem,
2013
10.
Dzhemilev U.M., D'yakonov V.A., Khafizova L.O., Ibragimov A.G.
Tetrahedron,
2004
11.
D'yakonov V.A., Makarov A.A., Ibragimov A.G., Khalilov L.M., Dzhemilev U.M.
Tetrahedron,
2008
12.
D'yakonov V.A., Makarov A.A., Makarova E.K., Dzhemilev U.M.
Tetrahedron,
2013
13.
Dzhemilev U.M., D’yakonov V.A., Khafizova L.O., Ibragimov A.G.
Russian Journal of Organic Chemistry,
2005
14.
D'yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.K., Khusnutdinova E.K., Dzhemilev U.M.
Chemical Communications,
2013
15.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Medicinal Chemistry Research,
2015
16.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Bioorganic and Medicinal Chemistry Letters,
2015
17.
D’yakonov V., Dzhemileva L., Makarov A., Mulyukova A., Baevd D., Khusnutdinova E., Tolstikova T., Dzhemilev U.
Current Cancer Drug Targets,
2015
18.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Tuktarova R.A., Islamov I.I., Dzhemilev U.M.
Russian Chemical Bulletin,
2015
19.
D’yakonov V.A., Makarov A.A., Makarova E.K., Khalilov L.M., Dzhemilev U.M.
Russian Chemical Bulletin,
2012
20.
Dzhemilev U.M., D’yakonov V.A., Tuktarova R.A., Dzhemileva L.U., Ishmukhametova S.R., Yunusbaeva M.M., de Meijere A.
Journal of Natural Products,
2016
21.
D'yakonov V.A., Tuktarova R.A., Ishmukhametova S.R., Dzhemilev U.M.
Tetrahedron,
2016
22.
Kuisle O., Quiñoá E., Riguera R.
Journal of Organic Chemistry,
1999
23.
Meyer S.D., Schreiber S.L.
Journal of Organic Chemistry,
1994