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A Concise Synthesis of (E)- and (Z)-Neomanoalides

Published in Helvetica chimica acta. 1994, vol. 77, no. 3, p. 661-667
Abstract The first synthesis of (Z)-neomanoalide (4) and an improved synthesis of its (E)-isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2-[(tert-butyl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]-methyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reaction with the (2Z)- or (2E)-isomer of (6E)-3-{[(tert-butyl)dimethylsiloxy]methyl}-7-methyl-9-(2′,6′,6′-trimethylcyclohex-1′-enyl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the corresponding neomanoalide.
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JEFFORD, Charles et al. A Concise Synthesis of (E)- and (Z)-Neomanoalides. In: Helvetica Chimica Acta, 1994, vol. 77, n° 3, p. 661-667. doi: 10.1002/hlca.19940770309 https://archive-ouverte.unige.ch/unige:84780

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