A concise route to dihydrobenzo[b]furans: formal total synthesis of (+)-lithospermic acid.
نویسندگان
چکیده
A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
منابع مشابه
Synthesis of anti-HIV lithospermic acid by two diverse strategies.
An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation to generate an appropriately substituted benzo[b]furan ester followed by a stereosel...
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ورودعنوان ژورنال:
- Organic letters
دوره 13 13 شماره
صفحات -
تاریخ انتشار 2011