474-07-7Relevant articles and documents
Synthetic method of brazilin natural product (+)-Brazilin
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Paragraph 0018; 0033, (2021/03/31)
The invention relates to a synthetic method of a brazilin natural product, namely (+)-Brazilin. According to the synthetic method, a compound 3,4-dimethoxybenzyl alcohol as shown in formula 1 is usedas an initial raw material and is subjected to a nucleophilic substitution reaction, a lithium aluminum hydride reduction reaction, a Lipase PS enzyme catalyzed desymmetry reaction and a Mitsunobu reaction a Dess-Martin oxidation reaction, a one-pot-process Prins/Friedel-Crafts cascade reaction under an acidic condition, and the like so as to synthesize the natural product (+)-Brazilin. Accordingto the invention, reagents used in the method are conventional chemical reagents, reaction conditions are mild, operation is easy, a rate is relatively high, reaction byproducts are few, and synthesissteps are greatly reduced, and therefore, synthesis cost is reduced to a large extent.
A total synthesis of (+)-brazilin
Huang, Shuangping,Ou, Wentao,Li, Wang,Xiao, Hesheng,Pang, Yiying,Zhou, Yi,Wang, Xiaoji,Yang, Xihua,Wang, Liping
, (2020/05/22)
Described herein is a concise total synthesis of (+)-brazilin from readily available 4-bromo-1,2-dimethoxybenzene. In this synthetic route, a Sharpless asymmetric dihydroxylation was employed to introduce the chiral hydroxyl group, and trifluoroacetic acid (TFA) catalyzed one-pot intramolecular tandem Prins/Friedel-Crafts reaction was also involved as the key transformation in the construction of the hybrid chromane and indane framework.
Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation
Arredondo, Vanessa,Roa, Daniel E.,Gutman, Eugene S.,Huynh, Nancy O.,Van Vranken, David L.
, p. 14745 - 14759 (2019/11/13)
Palladium-catalyzed carbene insertion was utilized in a formal synthesis of (±)-picropodophyllone and a total synthesis of (±)-brazilin. All prior syntheses of brazilin have involved a Friedel-Crafts alkylation in the key carbon-carbon bond forming events. The palladium-catalyzed [4 + 1] reaction generates a 1-arylindane with all of the functionalities needed for formation of the indano[2,1-c]chroman ring system of brazilin. The synthesis of (±)-brazilin was achieved in 11 steps (longest linear sequence) with an overall 11% yield.
Total synthesis of brazilin
Jung, Youngeun,Kim, Ikyon
, p. 2001 - 2005 (2015/02/19)
Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.
Formal synthesis of (±)-brazilin and total synthesis of (±)-brazilane
Yadav, Jhillu Singh,Mishra, Anand Kumar,Das, Saibal
, p. 7560 - 7566 (2014/12/10)
A convergent synthesis towards (±)-brazilin and (±)-brazilane has been reported from 3,4-dimethoxy benzaldehyde in A tetracyclic substituted indane common key intermediate is employed to furnish the desired two molecules in good to excellent yield. Pd(OH)2has played a crucial role in the total synthesis of (±)-brazilane.
Enantioselective syntheses of (+)- and (-)-brazilin
Javed, Umair,Karim, Moinul,Jahng, Katherine C.,Park, Jae-Gyu,Jahng, Yurngdong
, p. 1270 - 1274 (2015/02/02)
Two enantiomers of brazilin were prepared in 9 steps from 7-hydroxychroman-4-one using the AD-mix-α and AD-mix-β-directed enantioselective dihydroxylation of 3-(4-hydroxy-3-methoxyphenyl)-2H-chromen-7-ol as a key step.
Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and (+)-brazilide A
Wang, Xuequan,Zhang, Hongbin,Yang, Xiaodong,Zhao, Jingfeng,Pan, Chengxue
supporting information, p. 5405 - 5407 (2013/06/27)
An enantioselective strategy for the synthesis of (+)-brazilin, (-)-brazilein and (+)-brazilide A has been developed. A Lewis acid mediated lactonization established the novel fused bis-lactone core of brazilide A and finalized the first total synthesis of (+)-brazilide A.
Total synthesis of (±)-brazilin and formal synthesis of (±)-brazilein, (±)-brazilide A using m-CPBA
Li, Liang-Qun,Li, Ming-Ming,Wang, Kou,Qin, Hong-Bo
, p. 6029 - 6031 (2013/10/22)
Total synthesis of (±)-brazilin has been accomplished. m-CPBA epoxidation of allyl alcohol 10 and epoxy opening reaction mediated by m-chlorobenzoic acid, formed in situ as a byproduct, gave advanced intermediate diol 14. O-alkylation and cyclization gave phenol 6 which enabled the formal synthesis of (±)-brazilein and (±)-brazilide A.
Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents
Ishii, Hideki,Koyama, Hiroko,Hagiwara, Kyoji,Miura, Tomoyuki,Xue, Guangai,Hashimoto, Yoshie,Kitahara, Genta,Aida, Yoko,Suzuki, Masaaki
, p. 1469 - 1474 (2012/03/26)
SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16:1; >80:40 μM), stronger inhibition of nuclear import (0.5:1.3 μM), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 μM), human peripheral blood mononuclear cells (PMBCs) (30.1 μM: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16:1; 0.1:0.01 and >0.001 μM). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents.
Synthesis of (±)-brazilin using IBX
Huang, Yaodong,Zhang, Jinsong,Pettus, Thomas R. R.
, p. 5841 - 5844 (2007/10/03)
(Chemical Equation Presented) A short synthesis of (±)-brazilin is reported. This synthesis uses several interesting and underutilized transformations including a regioselective dirhodium-catalyzed aryl C-H insertion, a regioselective IBX phenol → o-quinone oxidation, a tautomerization of an o-quinone to a p-quinone methide, and an intramolecular aryl cyclization with a p-quinone methide.
