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DOI: 10.1055/s-0030-1258549
Cycloadditions of Allylsilanes - Part 22. [¹] Stereoselective Synthesis of Cyclopentanes and Cyclobutanes by Lewis Acid Promoted [3+2] and [2+2] Cycloadditions of Allylsilanes
Publikationsverlauf
Publikationsdatum:
30. August 2010 (online)
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Abstract
The development of Lewis acid promoted [3+2] and [2+2] cycloadditions as a novel methodology for the stereoselective construction of cyclopentanes and cyclobutanes is described. Elegant applications of this methodology to the total synthesis of biologically active terpenoid natural products are presented.
1 Introduction
2 [3+2] Cycloadditions of Allylsilanes
2.1 Synthesis of Silylbicyclo[n.3.0]alkanes
2.2 Synthesis of Silylcyclopentanes
2.3 Domino [3+2] Cycloadditions with Alkynones
2.4 [3+2] Cycloadditions with Cycloalkenones
2.5 Synthesis of Silylspirocyclopentanes
2.6 Asymmetric [3+2] Cycloadditions with Chiral Allylsilanes
3 Transformations of the Silylcyclopentanes
3.1 Conversion of the Silylbicyclo[n.3.0]alkanes into Symmetrical Olefins
3.2 Development of a Modified Fleming-Tamao Oxidation
4 Domino Double [3+2] Cycloaddition/Wagner-Meerwein Rearrangement/Friedel-Crafts Alkylation/Elimination
5 [2+2] Cycloadditions of Allylsilanes
5.1 Mechanism
5.2 Synthesis of (Silylmethyl)cyclobutanes
5.3 Rearrangement of (Silylmethyl)cyclobutanes to Silylcyclopentanes
5.4 Domino [2+2] Cycloadditions with Alkynoic Esters
5.5 Stereospecific [2+2] Cycloadditions
5.6 Modified Fleming-Tamao Oxidation of the (Silylmethyl)cyclobutanes
6 Applications to Natural Product Synthesis
6.1 Angular Triquinanes
6.1.1 (±)-Cameroonanol
6.1.2 (±)-Isocomene and (±)-β-Isocomene
6.2 Cyclobutane Natural Products
6.2.1 (±)-Fragranol
6.2.2 The Oleander Scale Pheromone
7 Conclusion
Key words
annulations - cycloadditions - enones - Lewis acids - silicon
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