Double diastereoselection in intramolecular photocycloadditions:: A radical rearrangement approach to the total synthesis of the spirovetivane phytoalexin (±)-lubiminol

被引：36

作者：

Crimmins, MT ^{[1
]}

Wang, Z ^{[1
]}

McKerlie, LA ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 08期

关键词：

D O I：

10.1021/ja973824y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly stereoselective total synthesis of the phytoalexin (+/-)-lubiminol (1) has been accomplished. The synthesis relies on three pivotal transformations: (1) a conjugate addition-cyclization reaction to prepare a highly functionalized 2-carbomethoxycyclopentenone as a photocycloaddition substrate, (2) a double diastereoselective intramolecular photocycloaddition for a stereoselective intramolecular photoaddition reaction which establishes the central quaternary spirocenter, and (3) the transformation of the photoadduct into the required spiro[5.4]decane through a radical fragmentation-rearrangement reaction.

引用

页码：1747 / 1756

页数：10

共 42 条

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