Abstract
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 ring segment 55 was achieved by the SmI 2 mediated reductive cyclization, constructing the EF ring bearing two 1,3-diaxial methyl groups, and the palladium catalyzed coupling of enol triflate and zinc bishomoenolate, making the GH ring moiety. Attempted convergent approaches toward the EFGH ring framework are also described.
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