A new reaction motif: "homo-S(N)2'-like" direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.

A new reaction motif: "homo-S(N)2'-like" direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.
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DOI:
10.1021/ja9056322
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发表时间:
2009-09-09
影响因子:
15
通讯作者:
Liebeskind, Lanny S.
Liebeskind, Lanny S.
中科院分区:
化学1区
文献类型:
--
作者:
Chen, Wenyong;Liebeskind, Lanny S.

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Charge neutral TpMo(CO)2(5-acyloxy-η3-pyranyl) and TpMo(CO)2(5-acyloxy-η3-pyridinyl) scaffolds undergo a novel intermolecular “homo-SN2′-like” reaction with a variety of carbon nucleophiles. Combined with an annulative demetalation, the homo-SN2′-like substitution/annulative demetalation sequence rapidly generates 2,7-dioxabicyclo[4.3.0]nonane and 2-aza-7-oxabicyclo[4.3.0]nonane frameworks in good to excellent yields with high enantiopurity. An enantiocontrolled total synthesis of the antimalarial alkaloid (+)-isofebrifugine was achieved utilizing this reaction cascade.
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