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三氟甲磺酸三乙锍（TESOTf）诱导的醌醇重排反应。通过发散-汇聚方法高效构建灰霉素的全功能化碳骨架。

TESOTf-induced rearrangement of quinols. Efficient construction of the fully functionalized carbon skeleton of the griseusins by a divergent-reconvergent approach.

作者信息

Parker Kathlyn A, Mindt Thomas L, Koh Yung-hyo

机构信息

Department of Chemistry, SUNY Stony Brook, Stony Brook, New York 11794-3400, USA.

出版信息

Org Lett. 2006 Apr 27;8(9):1759-62. doi: 10.1021/ol060206q.

DOI:10.1021/ol060206q
PMID:16623544
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2668545/
Abstract

[reaction: see text] The "reverse polarity" or "umpolung" strategy for the total synthesis of aryl C-glycosides was developed in the context of the antibiotic (-)-griseusin B. Although a key reaction in a model sequence for the total synthesis produced two structurally divergent products, both were converted to the same advanced model intermediate that contains the complete carbon skeleton and (except for the extraneous oxygen substituent in the model series) the functional group pattern of the griseusins.

摘要

[反应：见正文] 芳基C-糖苷全合成的“反极性”或“极性翻转”策略是在抗生素（-）-灰黄霉素B的背景下开发的。尽管全合成模型序列中的一个关键反应产生了两种结构不同的产物，但两者都被转化为相同的高级模型中间体，该中间体包含完整的碳骨架以及（除模型系列中的外来氧取代基外）灰黄霉素的官能团模式。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/73ea8052acb9/nihms60982f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/ea7f21e532dc/nihms60982f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/59fa9737a946/nihms60982f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/cefdd0114206/nihms60982f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/81354d879456/nihms60982f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/07898ac92705/nihms60982f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/73ea8052acb9/nihms60982f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/ea7f21e532dc/nihms60982f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/59fa9737a946/nihms60982f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/cefdd0114206/nihms60982f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/81354d879456/nihms60982f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/07898ac92705/nihms60982f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a4a/2668545/73ea8052acb9/nihms60982f6.jpg

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