Total synthesis of sporolide B and 9-epi-sporolide B.
Total synthesis of sporolide B and 9-epi-sporolide B.
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DOI：
10.1021/ja1048994
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发表时间：
2010-08-18
影响因子：
15
通讯作者：
Botta, Lorenzo
中科院分区：
文献类型：
--
作者：
Nicolaou, K. C.;Wang, Jianhua;Tang, Yefeng;Botta, Lorenzo
The total synthesis of the structurally unique secondary metabolite sporolide B (1b, Figure 1) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system toward a number of indene derivatives as dienophiles, first in intermolecular and thence intramolecular settings. Thus, substrates were devised (37, Scheme 5; 75, Scheme 11) that underwent exquisite intramolecular [4+2] cycloaddition reactions under thermal conditions to provide primitive sporolide-type structures that were subsequently elaborated to sporolide model system 4 (Figure 1), 9-epi-sporolide B (5, Figure 1), and sporolide B (1b). The requisite indene o-quinone precursor (75, Scheme 10) was synthesized through a rutheniumcatalyzed [2+2+2] cycloaddition reaction between a propargylic alcohol (42, Figure 8) and a chloroacetylenic cyclopentenyne (64, Scheme 9) followed by elaboration and silver-promoted oxidation of the resulting chloroindene derivative. In addition to the total synthesis of 1b, this work demonstrated, for the first time, the power of the intramolecular hetero [4+2] cycloaddition reaction in the total synthesis of complex molecules and the application of the ruthenium-catalyzed [2+2+2] cycloaddition reaction to highly substituted indene systems possessing a chlorine residue on the aromatic nucleus.
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影响因子：
2.1
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Henry, GD
通讯作者：
Henry, GD
影响因子：
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作者：
EVANS, DA;CHAPMAN, KT;CARREIRA, EM
通讯作者：
CARREIRA, EM
影响因子：
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Feling, RH;Buchanan, GO;Fenical, W
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Fenical, W
影响因子：
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Curran, TT;Hay, DA;Evans, JC
通讯作者：
Evans, JC
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Baran, PS;Burns, NZ
通讯作者：
Burns, NZ