370884-60-9Relevant articles and documents
Syntheses of the AB and EFGH ring segments of gambierol
Kadota, Isao,Kadowaki, Chie,Park, Choul-Hong,Takamura, Hiroyoshi,Sato, Kumi,Chan, Philip W.H,Thorand, Stephan,Yamamoto, Yoshinori
, p. 1799 - 1816 (2007/10/03)
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 SmI2 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.