Synthetic studies on nogalamycin congeners [3]1,2 total syntheses of (+)-nogarene, (+)-7-deoxynogarol,and (+)-7-con-o-methylnogarol |
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Affiliation: | 1. Department of Chemistry, University of North Bengal, Darjeeling 734013, West Bengal, India;2. Department of Chemistry, Raiganj University, Uttar Dinajpur 733134, West Bengal, India;3. Department of Chemistry, Bangabasi Morning College, Kolkata 700009, West Bengal, India |
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Abstract: | 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. |
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