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Stereocontrolled syntheses of the AB and EFGH ring systems of gambierol (1) are described. The two key intermediates 3 and 55, representing the AB and EFGH ring frameworks, were prepared from 2-deoxy-d-ribose via linear sequences. Brown's asymmetric allylboration and the intramolecular hetero-Michael reaction were successfully applied to the construction of the A ring moiety. Synthesis of the EFGH...
Palladium catalyzed addition of certain carbon pronucleophiles 2 to conjugated enynes 1 afforded the corresponding allenes 3 in good to excellent yields. The most reactive methynes such as methylmalononitrile 2c enabled to undergo double addition leading to alkenes 4. Catalyst optimization supported Pd 2 (dba) 3 CHCl 3 -dppf combination as the best system among all catalysts...
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