105827-62-1Relevant articles and documents
TOTAL SYNTHESES OF (+)-NOGARENE AND (+)-7,8-DIHYDRONOGARENE
Kawasaki, Motoji,Matsuda, Fuyuhiko,Terashima, Shiro
, p. 2145 - 2148 (1986)
Total syntheses of the title compounds, the simplest and the hitherto unknown novel nogalamycin congeners, were first accomplished by elaborating the CDEF-ring system (5) from the methyl ketone (6) and subjecting 5 to regioselective Diels-Alder reaction with the bistrimethylsilyl keteneacetal (22).
SYNTHETIC STUDIES ON NOGALAMYCIN CONGENERS ; TOTAL SYNTHESES OF (+)-NOGARENE, (+)-7-DEOXYNOGAROL, AND (+)-7-CON-O-METHYLNOGAROL
Kawasaki, Motoji,Matsuda, Fuyuhiko,Terashima, Shiro
, p. 5727 - 5744 (2007/10/02)
According to the retrosynthetic perspective, the title total syntheses were accomplished by employing the regioselective Diels-Alder reactions of the (+)-naphthoquinone (5), the CDEF-ring system of nogalamycin congeners, with various structural types of dienes (8, 16, and 26).The highly functionalized dienes (16 and 26) incorporating all the functionalities present in the A-rings of (+)-7-deoxynogarol (3) and (+)-7-con-O-methylnogarol (2), were prepared efficiently by way of the 1,4-cyclohexadiene and 2-cyclohexanone derivatives (6 and 21), respectively.Reaction mechanism of the key Diels-Alder reaction was also discussed in terms of its stereoselectivity.
