853750-58-0Relevant academic research and scientific papers
Total synthesis of (+)-virgatusin via AlCl3-catalyzed [3+2] cycloaddition
Sanders, Shanina D.,Ruiz-Olalla, Andrea,Johnson, Jeffrey S.
supporting information; experimental part, p. 5135 - 5137 (2009/12/08)
The AlCl3-catalyzed cycloaddition of a donor-acceptor (don-acc) cyclopropane and piperonal succinctly provides the core of virgatusin in a selective, high-yielding manner. The Royal Society of Chemistry 2009.
Stereocontrolled assembly of tetrasubstituted tetrahydrofurans: A concise synthesis of virgatusin
Akindele, Tito,Marsden, Stephen P.,Cumming, John G.
, p. 3685 - 3688 (2007/10/03)
(Chemical Equation Presented) The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and α,β-unsaturated aldehydes as substrates,
First enantioselective synthesis of (-)- And (+)-virgatusin, tetra-substituted tetrahydrofuran lignan
Yamauchi, Satoshi,Okazaki, Momotoshi,Akiyama, Koichi,Sugahara, Takuya,Kishida, Taro,Kashiwagi, Takehiro
, p. 1670 - 1675 (2007/10/03)
The first highly enantioselective syntheses of tetra-substituted tetrahydrofuran lignan, (-)- and (+)-virgatusin, were achieved. Hemiacetal 15 was stereoselectively obtained from Evans's syn-aldol product 8 as a single isomer. This hemiacetal 15 was converted to (-)-virgatusin via hydrogenolysis. (+)-Virgatusin was also synthesized through the same process. The enantiomeric excess of the both enantiomers was determined as more than 99% ee. The Royal Society of Chemistry 2005.
