硅氧基呋喃与苯并吡喃酮的乙烯基加成：一种构建四羟基蒽酮天然产物的简洁方法。
Vinylogous addition of siloxyfurans to benzopyryliums: a concise approach to the tetrahydroxanthone natural products.
机构信息
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, United States.
出版信息
J Am Chem Soc. 2011 Feb 16;133(6):1714-7. doi: 10.1021/ja110698n. Epub 2011 Jan 25.
Abstract
A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.
摘要
采用硅氧基呋喃的烯醇加成反应和后期的狄克曼环化反应，开发了一种简洁的四羟基蒽酮天然产物合成方法。利用这种方法，从 5-羟色酮底物出发，通过最多四步反应，就能立体选择性地合成手性、外消旋形式的天然产物 blennolide B 和 blennolide C。通过计算研究探究了烯醇加成的区域和立体选择性，这表明涉及到 Diels-Alder 类似的过渡态。
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