Total synthesis of two novel brominated acetylenic diols (+)-diplyne C and E: stereoselective construction of the (E)-1-bromo-1-alkene

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• 作者：Benjamin W. Gung ; Craig Gibeau and Amanda Jones
• 刊名：Tetrahedron: Asymmetry
• 出版年：2005
• 出版时间：2005
• 年：2005
• 卷：16
• 期：18
• 页码：3107-3114
• 全文大小：165 K

文摘

The total syntheses of the enantiomers of two novel brominated polyacetylenic natural products diplynes C and E are reported. Pd and Cu(I)-catalyzed coupling reactions were employed to synthesize the diyne and enyne units. The stereochemistry of the terminal (E)-alkenyl bromide in diplyne C was constructed stereoselectively using Brown’s hydroboration–bromination procedure. The stereochemistry of the internal (E)-double bond in diplyne E was established using a Takai reaction. The stereocenter was derived from d-mannitol.