کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5212275 | 1383110 | 2017 | 11 صفحه PDF | دانلود رایگان |
The total syntheses of (−)-amphirionin-4 and (+)-amphirionin-4 have been achieved in a convergent and enantioselective manner. The tetrahydrofuranol cores of amphirionin-4 were constructed in optically active form by enzymatic resolution of racemic cis-3-hydroxy-5-methyldihydrofuran-2(3H)-one. The polyene side chain was efficiently synthesized using Stille coupling. The remote C8-stereocenter was constructed using the Nozaki-Hiyama-Kishi coupling reaction. Detailed 1H NMR studies of Mosher esters of (−)-amphirionin-4 and (+)-amphirionin-4 were carried out to support the assignment of the absolute configurations of the C-4 and C-8 asymmetric centers of amphirionin-4.
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Journal: Tetrahedron - Volume 73, Issue 14, 6 April 2017, Pages 1820–1830