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具有S(2)-对称CD环核心的1α,25-二羟基维生素D类似物的合成。

Synthesis of 1alpha,25-dihydroxyvitamin D analogues featuring a S(2)-symmetric CD-ring core.

作者信息

Minne Garrett, Verlinden Lieve, Verstuyf Annemieke, De Clercq Pierre J

机构信息

Department of Organic Chemistry, Ghent University, Krijgslaan, Belgium.

出版信息

Molecules. 2009 Feb 24;14(2):894-903. doi: 10.3390/molecules14020894.

DOI:10.3390/molecules14020894
PMID:19255548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6254054/
Abstract

Three analogues of 1a,25-dihydroxyvitamin D(3) (calcitriol), featuring a trans-fused decalin C,D-core with local S(2)-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR,8aS)-octahydronaphthalene-1,5-dione (7). The very short sequences involve the simultaneous introduction of the side-chain and seco-B,A-ring fragments via Suzuki and Sonogashira coupling reactions. The analogues are devoid of relevant biological activity.

摘要

已从容易获得的(4aR,8aS)-八氢萘-1,5-二酮(7)出发，合成了三种1α,25-二羟基维生素D(3)(骨化三醇)类似物，其具有具有局部S(2)-对称性的反式稠合十氢化萘C、D核，且具有相同的侧链和开环B、A环结构。非常简短的合成路线涉及通过铃木和宗和反应同时引入侧链和开环B、A环片段。这些类似物没有相关的生物活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/7c82c38eee11/molecules-14-00894-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/0c51edaa85e8/molecules-14-00894-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/debd265cd58c/molecules-14-00894-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/ce231729045e/molecules-14-00894-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/c3106ff49dab/molecules-14-00894-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/7c82c38eee11/molecules-14-00894-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/0c51edaa85e8/molecules-14-00894-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/debd265cd58c/molecules-14-00894-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/ce231729045e/molecules-14-00894-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/c3106ff49dab/molecules-14-00894-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c164/6254054/7c82c38eee11/molecules-14-00894-g005.jpg

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