Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

Kim, Jin-Woo; Kim, Ikyon

doi:10.1039/c7ob02758c

Cited by 15 publications

(8 citation statements)

References 51 publications

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“…However, NMR analysis of the chromatographically isolated major product revealed that desired product 5 was contaminated with one or more minor impurities. Nevertheless, a one-pot triple O-demethylation of 5 with excess BBr 3 in CH 2 Cl 2 furnished 6 (the thia analogue of the natural product brazilane 11 ), which was significantly purer than 5, although traces of impurity (<5%) still remained with 5.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Das

2022

J. Org. Chem.

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Presented herein is a BF 3 •OEt 2 -mediated, diastereoselective one-pot double cyclization of 4-aryl-2-[(arylthio)methyl]butanals leading to the formation of cis-tetrahydro-6H-naphtho[2,1-c]thiochromenes for the first time. Mechanistically, the formation of the title products involves the one-pot intramolecular Friedel−Crafts hydroxyalkylation/intramolecular Friedel−Crafts alkylation cascade. This synthetic methodology is featured by its high atom economy, broad substrate scope, mild transition-metalfree reaction conditions, capability to assemble two new rings in one pot, and moderate to high yields (up to 94% yield). It was then applied in the synthesis of a thia analogue of brazilane and a chromeno[3,4-c]chromene derivative. Moreover, the methodology was successfully extended to the synthesis of cis-hexahydrobenzo[c]phenanthrenes. Specifically, 1,5-diarylpentan-3-ones were first subjected to the Corey−Chaykovsky reaction, and the resulting epoxides, without being chromatographically isolated, were treated with BF 3 •OEt 2 to afford the cyclized products in high yields (up to 84% yield over two steps).

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Section: ■ Results and Discussionmentioning

confidence: 99%

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Das

2022

J. Org. Chem.

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“…This is achieved through an intramolecular Friedel–Crafts acylation, followed by reduction, resulting in the formation of the brazilane ( 12 ) scaffold (Scheme 4). 60…”

Section: Syntheses Of Brazilin-type Homoisoflavonoidsmentioning

confidence: 99%

Advances in the synthesis of rearranged homoisoflavonoids

Demidoff,

Costa,

Caleffi

2024

Org. Biomol. Chem.

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“…The molecular formula of brazilin is C 16 H 14 O 5 , which is the main active component in C. sappan. A total of 13 brazilin metabolites (195)(196)(197)(198)(199)(200)(201)(202)(203)(204)(205)(206) have been isolated and identified (Xu et al, 1994;Shu et al, 2007;Hung et al, 2009;Cooksey, 2010;Wang and Liang, 2016;Kim and Kim, 2018). Brizilide is not a component naturally present in hematoxylin itself but rather a newly derived component that emerges during the isolation process from brazilin hematoxylin (Supplementary Figure S1).…”

Section: Brazilinmentioning

confidence: 99%

A comprehensive review of Shengdeng in Tibetan medicine: textual research, herbal and botanical distribution, traditional uses, phytochemistry, and pharmacology

Ma,

Li,

Wang

et al. 2023

Front. Pharmacol.

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“Shengdeng”, a group of Tibetan medicines with diverse biological origins, has long been utilized in Tibet for the treatment of rheumatoid arthritis. It showcases remarkable efficacy in alleviating rheumatism, reducing swelling, and relieving pain. This study aimed to clarify the plant species used as “Shengdeng” and summarize their botanical distribution, traditional uses, phytochemistry, and pharmacology to promote its utilization and development. “Shengdeng” is derived from a remarkable collection of 14 plant species belonging to six distinct families. Extensive phytochemical investigations have led to the identification of 355 chemical constituents within “Shengdeng”. Pharmacological studies conducted on “Shengdeng” have revealed a wide range of beneficial properties, including antioxidant, anticancer, antimicrobial, antiviral, antiparasitic, anti-inflammatory, and anti-arthritic activities. Notably, flavonoids and triterpenoids emerge as the predominant groups among these constituents, contributing to the therapeutic potential and diverse applications of “Shengdeng”. The present review provides a concise summary of the recent advancements in textual research concerning the herbal and botanical distribution, traditional uses, phytochemistry, and pharmacological activities of “Shengdeng”. It is crucial to note that future research on “Shengdeng” should prioritize the analysis of its active ingredients and the establishment of rigorous quality standards. These aspects are essential for ensuring consistency, efficacy, and safety in its clinical application.

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Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

Cited by 15 publications

References 51 publications

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Advances in the synthesis of rearranged homoisoflavonoids

A comprehensive review of Shengdeng in Tibetan medicine: textual research, herbal and botanical distribution, traditional uses, phytochemistry, and pharmacology

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