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在 Paternò-Büchi 二聚反应中形成大环内酯。

Formation of macrocyclic lactones in the Paternò-Büchi dimerization reaction.

机构信息

Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI), 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.

出版信息

Beilstein J Org Chem. 2011 Feb 28;7:265-9. doi: 10.3762/bjoc.7.35.

DOI:10.3762/bjoc.7.35
PMID:21448243
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3063007/
Abstract

Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C(i) symmetry including two oxetane-rings, which are the Paternò-Büchi dimerization products, were isolated in ca. 20% yield. The intramolecular cyclization products, such as 3-alkoxyoxetane and 2,7-dioxabicyclo[2.2.1]hept-5-ene derivatives, were not detected in the photolysate.

摘要

呋喃-2-基甲基 2-氧代乙酸酯 1a,b 是通过商业可得的呋喃-2-甲醇合成的，其中呋喃环和羰基部分被嵌入分子内，研究了它们的光化学反应（hν > 290nm）。十二元大环内酯 2a,b 具有 C(i)对称性，包含两个环氧乙烷环，是 Paternò-Büchi 二聚化产物，以约 20%的产率分离得到。在光解产物中未检测到分子内环化产物，如 3-烷氧基环氧乙烷和 2,7-二氧杂双环[2.2.1]庚-5-烯衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1185/3063007/7d152bee71a8/Beilstein_J_Org_Chem-07-265-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1185/3063007/96e2e2492797/Beilstein_J_Org_Chem-07-265-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1185/3063007/7d152bee71a8/Beilstein_J_Org_Chem-07-265-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1185/3063007/96e2e2492797/Beilstein_J_Org_Chem-07-265-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1185/3063007/7d152bee71a8/Beilstein_J_Org_Chem-07-265-g005.jpg

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J Am Chem Soc. 2010 Aug 25;132(33):11768-78. doi: 10.1021/ja1047363.
2
Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.硅烯转移至α-酮酯及其在γ-内酯合成中的应用。
Tetrahedron. 2009 Sep 1;65(33):6447-6453. doi: 10.1016/j.tet.2009.05.066.
3
Origin of a large temperature dependence of regioselectivity observed for [2 + 2] photocycloaddition (Paternò-Büchi reaction) of 1,3-dimethylthymine with benzophenone and its derivatives: conformational property of the intermediary triplet 1,4-diradicals.
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J Org Chem. 2005 Apr 1;70(7):2522-7. doi: 10.1021/jo048006k.
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Selectivity control in electron spin inversion processes: regio- and stereochemistry of Paternò-Büchi photocycloadditions as a powerful tool for mapping intersystem crossing processes.电子自旋反转过程中的选择性控制：Paternò-Büchi光环加成反应的区域化学和立体化学作为映射系间窜越过程的有力工具。
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