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

✍ Scribed by Margot Fink; Hans Gaier; Hans Gerlacho

Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 509 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650827

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✦ Synopsis

2,3‐Alkadienoates as Dienophiles, Application in the Synthesis of (+)‐(R)‐Lasiodiplodin

Methyl 2, 3‐alkadienoates 2 are shown to react at 80° with l, 1‐dimethoxy‐3trimethylsilyloxy‐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, CH~3~, C~6~H~5~). An analogous reaction sequence starting with (‐)‐(11 R)‐dodeca‐2, 3‐dien‐11‐olide ((‐)‐6) and 1 leads, via the adduct (R)‐7, to (+)‐(R)‐lasiodiplodin ((+)−8) with properties identical to those of the natural product. The allene lactone (‐)‐6 was prepared by an intramolecular Wittig condensation of (R)−5, produced from (–)‐(R)‐9‐hydroxydecanoic acid.

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