Iron-Mediated Complete Chirality Transfer in Allylic Substitutions. Efficient Synthesis of (-)-(S)-Myoporone

D. Enders; B. Jandeleit

doi:10.1055/s-1994-25689

Synthesis 1994; 1994(12): 1327-1330
DOI: 10.1055/s-1994-25689

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Iron-Mediated Complete Chirality Transfer in Allylic Substitutions. Efficient Synthesis of (-)-(S)-Myoporone

D. Enders^* , B. Jandeleit

^*Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany

Abstract

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The furanosesquiterpenoid (-)-(S)-myoporone [(S)-10], a toxic stress metabolite of sweet potatoes (Ipomoea batatas) and normal secondary metabolite of the australian shrub Myoporum deserti has been synthesized in high enantiomeric purity (ee > 99 %) and excellent overall yield. Key step in the synthesis is the regio- and stereocontrolled addition of the silyl enol ether 3 to the planar chiral tetracarbonyliron(1+) complex (1R,2S,3R)-2 easily obtained from (S)-lactic acid.

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