Formal total synthesis of fostriecin.
[reaction: see text] Addition of magnesium anion 4 (M = MgBr, R(1) = TES) to ketone 6 (R(2) = PMB) at -78 degrees C in THF proceeded under chelation control to provide alcohol 7, which possesses the full set of the chiral centers of fostriecin. Subsequently, 7 was transformed successfully to the known key intermediate 2.
Wang
Yong-Gang
YG
Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Kobayashi
Yuichi
Y
D000438:Alcohols; D000475:Alkenes / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D007659:Ketones / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry; D011753:Pyrones
D000438:Alcohols; D000475:Alkenes; D000903:Antibiotics, Antineoplastic; D004791:Enzyme Inhibitors; D007659:Ketones; D011090:Polyenes; D011753:Pyrones; D008274:Magnesium; C040313:fostriecin