Phosphine catalyzed [3+2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.
Der als Reaktionsprodukt des Dichloro‐Ni‐Komplexes (I) und des Na‐bis‐[disilylmethyl]‐phosphids (II) isolierten krist‐allinen Verbindung wird aufgrund 31P‐NMR‐spektroskopischer Untersuchungen, einer Einkristall‐Röntgendiffraktionsanalyse und von MO‐Betrachtungen die Struktur (III) zuerkannt.
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