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Issue 17, 1998
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Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (±)-dihydronepetalactone using the SE2′ reaction of an allylsilane

Abstract

A propargylic alcohol 24 with the propynyl group exo on the norbornene framework was used in a stereospecific synthesis of the mixture of allylsilanes 27 and 28. The stereospecific reaction of this mixture with peracid gave, with a high level of stereocontrol, the norbornenol 25 having the alkenyl group endo on the norbornene framework. This substrate underwent an oxyanion accelerated Cope rearrangement setting up all four stereocentres in a synthesis of (±)-dihydronepetalactone 6.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1998, 2645-2650
Article type
Paper

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (±)-dihydronepetalactone using the SE2′ reaction of an allylsilane

I. Fleming and N. K. Terrett, J. Chem. Soc., Perkin Trans. 1, 1998, 2645
DOI: 10.1039/A804268C

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