494760-63-3Relevant academic research and scientific papers
Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities
Kadota, Isao,Takamura, Hiroyoshi,Sato, Kumi,Ohno, Akio,Matsuda, Kumiko,Satake, Masayuki,Yamamoto, Yoshinori
, p. 11893 - 11899 (2007/10/03)
The convergent total syntheses of gambierol (1) and 16-epi-gambierol (2) have been achieved. The ABC and FGH ring segments 4 and 5 were prepared from known compounds 6 and 13, respectively, by linear manners. The fragments prepared were connected by our own synthetic strategy including the intramolecular allylation of α-acetoxy ether followed by ring-closing metathesis to furnish the octacyclic ether 3. The diiodoalkene 45, prepared from 3, was converted to the Z-iodoalkene 50 via a novel and stereoselective hydrogenolysis followed by deprotection. Construction of the triene side chain was performed by the modified Stille coupling of 50 with the Z-vinylic stannane 41 to afford 1. The similar transformations were carried out on the epimeric octacycle 34 to give 2, which showed no toxicity against mice at the concentration of 14 mg/kg.
Total synthesis of gambierol
Kadota, Isao,Takamura, Hiroyoshi,Sato, Kumi,Ohno, Akio,Matsuda, Kumiko,Yamamoto, Yoshinori
, p. 46 - 47 (2007/10/03)
The convergent total synthesis of gambierol (1) is described. The octacyclic ether framework of 1 was constructed via the intramolecular allylation of α-chloroacetoxy ether followed by ring-closing metathesis. A modified Stille coupling was successfully applied to the synthesis of the triene side chain. Copyright
