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B型酸浆苦素右侧结构的合成

Synthesis of the Right-Side Structure of Type B Physalins.

作者信息

Morita Masaki, Kojima Shuntaro, Ohkubo Megumi, Koshino Hiroyuki, Hashizume Daisuke, Hirai Go, Maruoka Keiji, Sodeoka Mikiko

机构信息

Synthetic Organic Chemistry Laboratory RIKEN2-1 Hirosawa Wako Saitama 351-0198 Japan.

AMED-CREST2-1 Hirosawa Wako Saitama 351-0198 Japan.

出版信息

Isr J Chem. 2017 Apr;57(3-4):309-318. doi: 10.1002/ijch.201600110. Epub 2016 Nov 9.

DOI:10.1002/ijch.201600110
PMID:28659646
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5467525/
Abstract

We present a full account of our synthetic studies on the racemic DEFGH-ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of the 2,3-Wittig rearrangement and methylation steps. Furthermore, we have newly established a method for the preparation of an optically active synthetic intermediate by enzymatic kinetic resolution. Our work provides access to both natural and nonnatural right-side physalin structures.

摘要

我们全面阐述了对酸浆苦素外消旋DEFGH环部分的合成研究，其特点是三环关键中间体的多米诺环转化。我们还报告了多米诺环转化详细机理研究的结果，以及2,3-维蒂希重排和甲基化步骤的重新优化。此外，我们新建立了一种通过酶促动力学拆分制备光学活性合成中间体的方法。我们的工作为天然和非天然右侧酸浆苦素结构的获取提供了途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/04ddc59aa7e2/IJCH-57-309-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b4b807cb2417/IJCH-57-309-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/39b600779cb0/IJCH-57-309-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/8c0886148854/IJCH-57-309-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/d8b982bb21f0/IJCH-57-309-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/ebe5492765d8/IJCH-57-309-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/12e635170daa/IJCH-57-309-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/70981dffef76/IJCH-57-309-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/0f0859877fd8/IJCH-57-309-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/c1052225d140/IJCH-57-309-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b8357024fe31/IJCH-57-309-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b6badc2733de/IJCH-57-309-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/8d72dafeb568/IJCH-57-309-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/f599959e4299/IJCH-57-309-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/d3c704d6932d/IJCH-57-309-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/04ddc59aa7e2/IJCH-57-309-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b4b807cb2417/IJCH-57-309-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/39b600779cb0/IJCH-57-309-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/8c0886148854/IJCH-57-309-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/d8b982bb21f0/IJCH-57-309-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/ebe5492765d8/IJCH-57-309-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/12e635170daa/IJCH-57-309-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/70981dffef76/IJCH-57-309-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/0f0859877fd8/IJCH-57-309-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/c1052225d140/IJCH-57-309-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b8357024fe31/IJCH-57-309-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/b6badc2733de/IJCH-57-309-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/8d72dafeb568/IJCH-57-309-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/f599959e4299/IJCH-57-309-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/d3c704d6932d/IJCH-57-309-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/282c/5467525/04ddc59aa7e2/IJCH-57-309-g015.jpg

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Org Lett. 2012 Jul 6;14(13):3434-7. doi: 10.1021/ol301394b. Epub 2012 Jun 15.
3
Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors.
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Steroids. 2012 Apr;77(5):441-7. doi: 10.1016/j.steroids.2011.11.016. Epub 2011 Dec 9.
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Carboxylate-directed tandem functionalisations of α,β-dihaloalkenoic acids with 1-alkynes: a straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides.α,β-二卤代链烯酸与1-炔烃的羧酸盐导向串联官能团化反应：一种直接合成(Z)-构型的α,β-取代γ-亚烷基丁烯内酯的方法。
Chemistry. 2011 Dec 2;17(49):13692-6. doi: 10.1002/chem.201102570. Epub 2011 Nov 7.
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