Tetrahedron p. 8905 - 8914 (1999)
Update date:2022-09-26
Topics:
Martin, Stephen F.
Bur, Scott K.
A concise synthesis of (-)-3, a known precursor of pumiliotoxin 251D, has been completed using a vinylogous Mannich reaction as a key construction. Silyloxyfuran 10 added to methoxypyrrolidine 20 in the presence of TMS-OTf to give a mixture (4.8:1) of 21 and 22 in 57% yield. Reduction and global deprotection of 21 afforded the bicyclic lactam 23. Raney Nickel mediated extrusion of the hydroxymethyl group from 23 gave (-)-3.
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Doi:10.1016/S0968-0896(99)00064-4
(1999)Doi:10.1016/S0277-5387(99)00105-9
(1999)Doi:10.1021/om9905005
(1999)Doi:10.1039/a902224d
(1999)Doi:10.1016/j.cclet.2021.01.018
(2021)Doi:10.1016/S0022-328X(00)91414-1
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