SYNTHETIC APPLICATIONS OF IMIDOTITANIUM ALKYNE [2+2] CYCLOADDITIONS - A CONCISE, STEREOCONTROLLED TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN

SYNTHETIC APPLICATIONS OF IMIDOTITANIUM ALKYNE [2+2] CYCLOADDITIONS - A CONCISE, STEREOCONTROLLED TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN
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DOI:
10.1021/ja00077a053
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发表时间:
1993-12-01
影响因子:
15
通讯作者:
LIVINGHOUSE, T
LIVINGHOUSE, T
中科院分区:
化学1区
文献类型:
--
作者:
MCGRANE, PL;LIVINGHOUSE, T

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通过收敛的分子内咪唑-乙炔[2+2]环加成-酰基氰化物缩合反应,实现了(+)-Preussin的高效立体选择性全合成(2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol(1)。
An efficient stereoselective total synthesis of (+)-preussin, (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol (1), was achieved by way of a convergent, intramolecular imidotitanium-alkyne [2 + 2] cycloaddition-acyl cyanide condensation sequence.