23221-90-1

Upstream product

• 102067-87-8 (3RS,4RS)-3-(3,4-dihydroxybenzyl)-3,4,7-trihydroxychroman <(+/-)-episappanol> 
• 102067-87-8 (3RS,4SR)-3-(3,4-dihydroxybenzyl)-3,4,7-trihydroxychroman <(+/-)-sappanol> 
• 873946-57-7 2-(3-benzyloxy-phenoxymethyl)-indan-2,5-diol 
• 96710-40-6 3-<3,4-Dibenzyloxy-benzyliden>-7-benzyloxy-chromanon-(4) 
• 104778-14-5 Sappanone A 
• 105341-83-1 C₃₇H₃₀O₆ 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6258-35-1 3-(3,4-dimethoxyphenyl)prop-2-yn-1-ol 
• 37899-29-9 O-trimethylbrazilin (3,9,10-trimethoxy-7,11b-dihydroindeno-[2,1-c]chromen-6a(6H)-ol) 

Downstream Products

• 474-07-7 (+)-(6ar,11bc)-7,11b-dihydro-indeno[2,1-c]chromene-3,6a,9,10-tetraol 
• 2241-61-4 (+/-)-Brasilin-tetraacetat 
• 600-76-0 brazilein 
• 176222-27-8 (6aR,11bR)-3,9,10-Tris-benzyloxy-6,6a,7,11b-tetrahydro-indeno[2,1-c]chromene 
• 176222-26-7 Thiocarbonic acid O-pentafluorophenyl ester O-((6aS,11bR)-3,9,10-tris-benzyloxy-7,11b-dihydro-indeno[2,1-c]chromen-6a-yl) ester 
• 176302-39-9 Thiocarbonic acid O-phenyl ester O-((6aS,11bR)-3,9,10-tris-benzyloxy-7,11b-dihydro-indeno[2,1-c]chromen-6a-yl) ester 
• 176222-28-9 Oxalic acid methyl ester (6aS,11bR)-3,9,10-tris-benzyloxy-7,11b-dihydro-indeno[2,1-c]chromen-6a-yl ester 
• 149862-29-3 3,9,10-Tris-benzyloxy-6,7-dihydro-indeno[2,1-c]chromene 
• 176302-38-8 (6aS,11bR)-3,9,10-Tris-benzyloxy-7,11b-dihydro-indeno[2,1-c]chromen-6a-ol 

Relevant academic research and scientific papers

A total synthesis of (+)-brazilin

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

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

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.

Total synthesis of (±)-brazilin and formal synthesis of (±)-brazilein, (±)-brazilide A using m-CPBA

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.

Synthetic method of brazilin natural product (+)-Brazilin

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.

Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation

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.

Enantioselective syntheses of (+)- and (-)-brazilin

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

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.

Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents

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

(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.