Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl-gamma-butyrolactone

Tan Z; Negishi E

首页> 外文期刊>Organic letters >Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl-gamma-butyrolactone

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Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl-gamma-butyrolactone

机译：具有高效结构的（Z）-2-碘-2-丁烯酸甲酯和（2R，3S，4S）-2-三甲基甲硅烷基-2,3-环氧-4-甲基-γ-丁内酯的高效合成的依帕内烯的选择性合成

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(+)-Epolactaene was synthesized in 14 steps in the longest linear sequence. The synthesis is highlighted by a highly efficient preparation of the lactone intermediate 4, which only requires three steps from the commercially available (S)-3-butyn-2-ol. It also features a fully stereocontrolled synthesis of the intermediate 9, which was constructed through the use of Zr-catalyzed methylalumination of alkynes and a series of Pd-catalyzed organozinc cross-coupling reactions, such as homopropargylation, direct ethynylation, and alkenylation of the methyl ester of (Z)-alpha-iodocrotonic acid (3).

机译：（+）-Epoactaene以最长的线性顺序分14步合成。内酯中间体4的高效制备突显了该合成过程，从市售（S）-3-butyn-2-ol只需三步。它还具有中间体9的完全立体控制合成，该中间体是通过使用Zr催化的炔烃甲基铝化和一系列Pd催化的有机锌交叉偶联反应（如均炔丙基化，直接乙炔化和甲基的烯基化）构建的（Z）-α-iodocrotonicacid（3）的酯。

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《Organic letters》 |2006年第13期|共3页
作者
Tan Z; Negishi E;
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正文语种 eng
中图分类有机化学;
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HUMAN NEUROBLASTOMA-CELLS; CONVERGENT TOTAL-SYNTHESIS; OXIRANYL ANION STRATEGY; ALPHA-ALKENYLATION; CONTROLLED CARBOMETALATION; NEURITOGENIC COMPOUND; REAGENTS; HALIDES; ROUTE; DERIVATIVES;

机译：人神经母细胞;聚合全合成;环氧乙烷阴离子策略;α-烯化;可控制的炭化;神经原性化合物;试剂;卤化物;路线;衍生物;

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1. Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl-gamma-butyrolactone [J] . Tan Z, Negishi E Organic letters . 2006,第13期

机译：具有高效结构的（Z）-2-碘-2-丁烯酸酯和（2R，3S，4S）-2-三甲基甲硅烷基-2,3-环氧-4-甲基-γ-丁内酯的高效合成选择性
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7. Selective Synthesis of Epolactaene Featuring Efficient Construction of Methyl (Z)-2-Iodo-2-butenoate and (2R, 3S, 4S)-2-Trimethylsilyl-2, 3-epoxy-4-methyl-g-butyrolactone [O] . -1

机译：选择性合成Epolactaene的高效构建（Z）-2-碘-2-丁酸甲酯和（2R，3S，4S）-2-三甲基甲硅烷基-2,3-环氧-4-甲基-G-丁内酯

Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl-gamma-butyrolactone

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