Helvetica Chimica Acta

2, 3??Alkadiensäureester als Dienophile; Anwendung bei der Synthese von (+)??(R)??Lasiodiplodin

M Fink, H Gaier, H Gerlacho

Index: Fink, Margot; Gaier, Hans; Gerlach, Hans Helvetica Chimica Acta, 1982 , vol. 65, # 8 p. 2563 - 2569

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Citation Number: 33

Abstract

Summary Methyl 2, 3-alkadienoates 2 are shown to react at 80" with 1, l-dimethoxy-3- trimethylsilyloxy-l, 3-butadiene (1) to give the adducts 3 in good yields. Rearrangement of 3, catalyzed by p-toluenesulfonic acid or by sodium methoxide, affords the 6-substituted methyl 4-hydroxy-2-methoxybenzoates 4 (R= H, CH3, C6H5). An analogous reaction sequence starting with (-)-(1 1 R)-dodeca-2, 3-dien-l1-olide ((-)-6) and 1 leads, via the adduct (R)-7, ...