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首页> 外文会议>American Chemical Society(ACS) National Meeting; 20000326-20000330; San Francisco,CA; US >Sugar-Derived Building Blocks for the Synthesis of Non-Carbohydrate Natural Products
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Sugar-Derived Building Blocks for the Synthesis of Non-Carbohydrate Natural Products

机译：糖类合成非碳水化合物天然产物的构建基块

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摘要

The generation of enantiopure non-carbohydrate natural products from readily available sugars is of practical value only, if the individual reactions employed allow simple reagents, proceed uniformly, and avoid complex separations in work-up procedures to ultimately enable favorable overall yields. Such practical criteria entail the transformation of a sugar, "overfunctionalized" with chirality and hydroxyl groups, into an enantiopure building block with suitable functionalities, e.g. C=C or C=O groups, or both, and only one or two centers of asymmetry left. The principal possibilities for the elaboration of new benign reaction channels sugar → enantiopure building block are delineated with an emphasis on dihydropyranones with isolated or vicinal centers of chirality, as they provide a more clearly foreseeable stereochemistry in additions of O-, N- and C-nucleophiles than their open-chain or furanoid counterparts. Application of various of such hexose-derived six-carbon building blocks to the synthesis of diplodialide-type pheromones, of the soft coral metabolites (S,S)-palythazin and (S,S)-bissetone, of ACRL-Toxin, of a series of Lab iatea- derived C_(12)-enelactones, and of uscharidine-type cardenolides is presented.
机译：如果所采用的各个反应允许使用简单的试剂，均匀进行且避免在后处理程序中进行复杂的分离以最终获得有利的总收率，则由易得的糖类生成对映纯的非碳水化合物天然产物仅具有实用价值。这样的实用标准要求将具有手性和羟基的“过度官能化”的糖转化为具有合适官能度的对映纯结构单元，例如对映体。 C ＝ C或C ＝ O基团，或两者兼有，仅剩下一个或两个不对称中心。阐述了新的良性反应通道糖→对映体纯结构单元的主要可能性，重点是具有手性或手性中心的二氢吡喃酮，因为它们除了O-，N-和C-外还提供了更清晰可预见的立体化学。亲核试剂比它们的开链或呋喃类似物好。各种此类己糖衍生的六碳结构单元在ACRL毒素的软珊瑚代谢物（S，S）-哌嗪和（S，S）-双西酮的双双环内酯型信息素的合成中的应用介绍了Lab iatea衍生的C_（12）-烯内酯系列和uscharidine型烯醇内酯的系列。

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