合成蜂毒素的 WXYZA' 结构域。
Synthesis of the WXYZA' domain of maitotoxin.
机构信息
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
出版信息
J Am Chem Soc. 2011 Jan 19;133(2):220-6. doi: 10.1021/ja109533y. Epub 2010 Dec 17.
Abstract
A synthesis of the WXYZA' domain (7) of the marine neurotoxin maitotoxin (1) is reported. The convergent synthetic strategy involves construction of key building blocks 11 and 12, their coupling, and the elaboration of the resulting ester (10) to the target molecule through a ring-closing metathesis and a hydroxy dithioketal cyclization as the key steps. For the construction of fragment 11, the Noyori reduction/Achmatowicz rearrangement and hydroxy epoxide opening technologies were applied (starting from furfuryl alcohol (13)), whereas for the synthesis of fragment 12, a carbohydrate-based approach was adopted (starting from 2-deoxy-D-ribose (14)). The synthesized WXYZA' domain (7) of maitotoxin (1) exhibited the expected (13)C NMR chemical shifts, supporting the originally assigned structure of the corresponding region of the natural product.
摘要
报道了海洋神经毒素马托毒素（1）的 WXYZA' 结构域（7）的综合。该综合的策略涉及关键构建块 11 和 12 的构建、它们的偶联以及通过闭环复分解和羟基二硫缩醛环化作为关键步骤将所得酯（10）精心设计到目标分子中。对于片段 11 的构建，应用了 Noyori 还原/Achmatowicz 重排和羟基环氧化物开环技术（从糠醇（13）开始），而对于片段 12 的合成，则采用了基于碳水化合物的方法（从 2-脱氧-D-核糖（14）开始）。合成的马托毒素（1）的 WXYZA' 结构域（7）表现出预期的（13）C NMR 化学位移，支持天然产物相应区域的原始结构。
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