Methods for Pyranoannulation: An Approach to a New Class of Polyethers.
Methods for Pyranoannulation: An Approach to a New Class of Polyethers.
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吡喃环化方法：一种新型聚醚的方法。
DOI：
10.1021/jo00216a049
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发表时间：
1985
期刊：
影响因子：
--
通讯作者：
Ghosh,ArunK
中科院分区：
文献类型：
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作者：
Kozikowski,AlanP;Ghosh,ArunK
已经开发了几种方法来将吡喃环融合到现有的吡喃环结构上，使得环上的氧呈现邻近的(乙二醇)关系。三环结构13，一种以前未知的物质，是通过这些方法的组合制备的。主席先生：在研究海洋天然产品短杆菌毒素B所呈现的独特结构时，1我们惊讶于这样一个事实，即人们也许可以通过一个涉及重复的吡喃(或更大的氧环)环化反应的方案在实验室组装这样的化合物。因此，我们寻求开发将吡喃环与现有的吡喃环结构环化的方法。我们在此公开了基于(A)二氢吡喃的环金属化/烷基化，(B)S-内酯的格氏加成，以及(C)碳水化合物或二乙酰氧基吡喃的异构烯丙基化来实现这一点的方法。
Several methods have been developed for fusing a pyran ring to an existing pyran ring structure such that the ring oxygens assume a vicinal (ethylene glycol) relationship. The tricyclic structure 13, a previously un-known substance, was prepared through a combination of these methods.Sir: In examining the unique structure presented by the marine natural product brevetoxin B, 1 we were struck by the fact that one could perhaps assemble such a compound in the laboratory through a scheme involving repetitive pyrano (or larger oxygen ring) annulation reactions. Accordingly, we have sought to develop methods for effecting the annulation of a pyran ring to an existing pyran ring structure. We disclose herein methods for accomplishing this which are based on (a) the ring metalation/alkylation of a dihydropyran,(b) Grignard addition to a S-lactone, and (c) the anomeric allylation of a carbohydrate or diacetoxypyran.