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Synlett 1998; 1998(2): 115-121
DOI: 10.1055/s-1998-1585
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Enyne Coupling as the Potent Methodology for the Synthesis of Bioactive Molecules

Xiyan Lu* , Guoxin Zhu, Zhong Wang
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China; Fax 86-21-64 16 61 28
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Publication Date:
31 December 2000 (online)

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The enyne coupling methodology for the synthesis of various sorts of substituted γ-butyrolactones from allylic alkynoates under the catalysis of PdX2 was developed. For α,β,γ-trisubstituted γ-butyrolactones, the β,γ-relative stereochemistry can be controlled by the substituent on the triple bond of the alkynoates and a chiral center is easily introduced from the optically active allylic alcohols. For α,β-disubstituted γ-butyrolactones, the optically active products can be obtained by the resolution of the key intermediates, lactonic aldehydes, via their tartrate acetal derivatives.

palladium catalyst - enyne coupling - allylic alkynoates - lactones - stereoselective