Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

doi:10.1007/s13659-024-00450-2

应用天然产物 ›› 2024, Vol. 14 ›› Issue (4): 29-29.DOI: 10.1007/s13659-024-00450-2

• ORIGINAL ARTICLES • 上一篇下一篇

Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

Xin-Ting Hu¹, Qing-Yan Cheng¹, Yan-Ping Chen¹, Kun Li¹, Cai-Xian Yan², Dashan Li¹, Li-Dong Shao¹

1. Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming 650500, China;
2. Yunnan Precious Metals Laboratory, Kunming Institute of Precious Metals, Kunming 650106, China

收稿日期:2024-03-21 发布日期:2024-08-01
通讯作者: Li-Dong Shao,E-mail:shaolidong@ynucm.edu.cn
基金资助:
The authors are grateful to the financial support from National Natural Science Foundation of China (82260683 and 22267024), Scientific and Technological Project of Yunnan Precious Metals Laboratory (YPML-2023050265 and YPML-2023050217), Yunnan Science and Technology Talent and Platform Program (202105AG070012), the Top Young Talent of Ten Thousand Talents Program of Yunnan Province (D. L. and L.-D. S.), the Start-up Fund of Yunnan University of Chinese Medicine (2019YZG03), and the Bioactive Ethnopharmacol Molecules Chemical Conversion and Application Innovation Team of Department of Education of Yunnan Province (2022).

Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

Xin-Ting Hu¹, Qing-Yan Cheng¹, Yan-Ping Chen¹, Kun Li¹, Cai-Xian Yan², Dashan Li¹, Li-Dong Shao¹

1. Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming 650500, China;
2. Yunnan Precious Metals Laboratory, Kunming Institute of Precious Metals, Kunming 650106, China

Received:2024-03-21 Published:2024-08-01
Contact: Li-Dong Shao,E-mail:shaolidong@ynucm.edu.cn
Supported by:
The authors are grateful to the financial support from National Natural Science Foundation of China (82260683 and 22267024), Scientific and Technological Project of Yunnan Precious Metals Laboratory (YPML-2023050265 and YPML-2023050217), Yunnan Science and Technology Talent and Platform Program (202105AG070012), the Top Young Talent of Ten Thousand Talents Program of Yunnan Province (D. L. and L.-D. S.), the Start-up Fund of Yunnan University of Chinese Medicine (2019YZG03), and the Bioactive Ethnopharmacol Molecules Chemical Conversion and Application Innovation Team of Department of Education of Yunnan Province (2022).

摘要/Abstract

摘要： A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes7 in 14-88% yields. Take advantage of the synthetic intermediate7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel-Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel-Crafts reactions.

关键词: Catalytic Prins reaction, Hydroxymethylation/hydroxylation, 1,3-Diarylpropene, Brazilin

Abstract: A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes7 in 14-88% yields. Take advantage of the synthetic intermediate7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel-Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel-Crafts reactions.

Key words: Catalytic Prins reaction, Hydroxymethylation/hydroxylation, 1,3-Diarylpropene, Brazilin

Xin-Ting Hu, Qing-Yan Cheng, Yan-Ping Chen, Kun Li, Cai-Xian Yan, Dashan Li, Li-Dong Shao. Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core[J]. 应用天然产物, 2024, 14(4): 29-29.

参考文献

[1] Lin L-G, Liu Q-Y, Ye Y. Naturally occurring homoisoflavonoids and their pharmacological activities. Planta Med. 2014;80:1053-66.
[2] Min BS, Cuong TD, Hung TM, Min BK, Shin BS, Woo MH. Compounds from the heartwood of Caesalpinia sappan and their anti-inflammatory activity. Bioorg Med Chem Lett. 2012;22:7436-9.
[3] Moon C-K, Lee SH, Lee MO, Kim SG. Effects of brazilin on glucose oxidation, lipogenesis and therein involved enzymes in adipose tissues from diabetic KK-mice. Life Sci. 1993;53:1291-7.
[4] Kim B, Kim S-H, Jeong S-J, Sohn EJ, Jung JH, Lee MH, Kim S-H. Brazilin induces apoptosis and G2/M arrest via inactivation of histone deacetylase in multiple myeloma U266 cells. J Agric Food Chem. 2012;60:9882-9.
[5] Lin L-G, Xie H, Li H-L, Tong L-J, Tang C-P, Ke C-Q, Liu Q-F, Lin L-P, Geng M-Y, Jiang H, Zhao W-M, Ding J, Ye Y. Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening. J Med Chem. 2008;51:4419-29.
[6] Javed U, Karim M, Jahng KC, Park J-G, Jahng Y. Enantioselective syntheses of (+)- and (-)-brazilin, Tetrahedron. Asymmetry. 2014;25:1270-4.
[7] Jung Y, Kim I. Total synthesis of brazilin. J Org Chem. 2015;80:2001-5.
[8] Jung Y, Kim I. A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation. Org Biomol Chem. 2015;13:4331-5.
[9] Gogoi D, Devi R, Pahari P, Sarma B, Das SK. cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin. Beilstein J Org Chem. 2016;12:2816-22.
[10] Huang Y, Zhang J, Pettus TRR. Synthesis of (±)-brazilin using IBX. Org Lett. 2005;7:5841-4.
[11] Pan C, Zeng X, Guan Y, Jiang X, Li L, Zhang H. Design and synthesis of brazilin-like compounds. Synlett. 2011;2011:425-9.
[12] Wang X, Zhang H, Yang X, Zhao J, Pan C. Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and (+)-brazilide A. Chem Commun. 2013;49:5405-7.
[13] Yadav JS, Mishra AK, Das S. Formal synthesis of (±)-brazilin and total synthesis of (±)-brazilane. Tetrahedron. 2014;70:7560-6.
[14] Arredondo V, Roa DE, Gutman ES, Huynh NO, Van Vranken DL. Total synthesis of (±)-brazilin using[4 + 1] palladium-catalyzed carbenylative annulation. J Org Chem. 2019;84:14745-59.
[15] Lin C-C, Teng T-M, Tsai C-C, Liao H-Y, Liu R-S. Gold-catalyzed deoxygenative nazarov cyclization of 2,4-dien-1-als for stereoselective synthesis of highly substituted cyclopentenes. J Am Chem Soc. 2008;130:16417-23.
[16] Huang S, Ou W, Li W, Xiao H, Pang Y, Zhou Y, Wang X, Yang X, Wang L. A total synthesis of (+)-brazilin. Tetrahedron Lett. 2020;61: 152052.
[17] Wang X, Liu W, Duan S, Yang X, Zhang H. Research progress on the synthesis of brazilin-type natural products. Chin J Org Chem. 2015;35:1585-97.
[18] Kim J, Kim I. Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane. Org Biomol Chem. 2018;16:89-100.
[19] Grimm JAA, Zhou H, Properzi R, Leutzsch M, Bistoni G, Nienhaus J, List B. Catalytic asymmetric synthesis of cannabinoids and menthol from neral. Nature. 2023;615:634-9.
[20] Díaz-Oviedo CD, Maji R, List B. The catalytic asymmetric intermolecular prins reaction. J Am Chem Soc. 2021;143:20598-604.
[21] Peng B, Ma J, Guo J, Gong Y, Wang R, Zhang Y, Zeng J, Chen W-W, Ding K, Zhao B. A powerful chiral super brønsted C-H acid for asymmetric catalysis. J Am Chem Soc. 2022;144:2853-60.
[22] Zhan R, Li D, Liu Y-L, Xie X-Y, Chen L, Shao L-D, Wang W-J, Chen Y-G. Structural elucidation, bio-inspired synthesis, and biological activities of cyclic diarylpropanes from Horsfieldia kingii. Tetrahedron. 2020;76: 131494.
[23] Yang B, Dong K, Li X-S, Wu L-Z, Liu Q. Photoacid-enabled synthesis of indanes via formal[3 + 2] cycloaddition of benzyl alcohols with olefins. Org Lett. 2022;24:2040-4.
[24] Zhang Z-J, Zhou X, Li D, Chen Y, Xiao W-W, Li R-T, Shao L-D. Aerobic copper-catalyzed intramolecular cascade oxidative isomerization/[4 + 4] cyclization of 2,2'-disubstituted stilbenes. J Org Chem. 2021;86:7609-24.
[25] Wang M, Liu Y-L, Li D, Xiao W-W, Chen Y, Zhang H-L, Zhan R, Shao L-D. Biomimetic synthesis and anti-inflammatory effects of horsfiequinone A. Tetrahedron Lett. 2021;65: 152756.

Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

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