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

A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane.

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Structure-based synthesis: From natural products to drug prototypes

Pure and Applied Chemistry ◽

10.1351/pac-con-08-07-12 ◽

2009 ◽

Vol 81 (6) ◽

pp. 1085-1091 ◽

Cited By ~ 4

Author(s):

Stephen Hanessian

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Design Element ◽

X Ray ◽

Design And Synthesis ◽

Highly Active ◽

In Vitro Inhibition ◽

Inhibitory Activities ◽

Active Natural

X-ray crystallographic data available from complexes of natural and synthetic molecules with the enzyme thrombin has led to the design and synthesis of truncated and hydrid molecules exhibiting excellent inhibition in vitro. The design element has also been extended to the synthesis and in vitro inhibition of a series of achiral molecules deploying aromatic and heterocyclic core motifs with appropriately functionalized appendages that provide excellent binding interactions at the S1, S2, and S3 sites of thrombin. Excellent selectivity for thrombin over trypsin has also been observed. Thus, studies in total synthesis of highly active natural aeruginosins have inspired further work toward truncated and hybrid analogs with excellent inhibitory activities. Structure-based organic synthesis has guided our research from natural products toward unnatural drug-like prototypes.

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Total synthesis of pyranonaphthoquinone natural products

10.31274/rtd-180813-12358 ◽

1994 ◽

Author(s):

Jun Li

Keyword(s):

Natural Products ◽

Total Synthesis

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Application of Dess-Martin oxidation in total synthesis of natural products

Current Organic Synthesis ◽

10.2174/1570179417666200917102634 ◽

2020 ◽

Vol 17 ◽

Author(s):

Majid M. Heravi ◽

Tayebe Momeni ◽

Vahideh Zadsirjan ◽

Leila Mohammadi

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Selective Oxidation ◽

Secondary Alcohols ◽

Aldehydes And Ketones

: Dess–Martin periodinane (DMP), is a commercially available chemical, frequently being utilized as a mild oxidative agent for the selective oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. DMP shows several merits over other common oxidative agent such as chromium- and DMSO-based oxidants, thus it is habitually employed in the total synthesis of natural products. In this review, we try to underscore the applications of DMP as an effective oxidant in an appropriate step (steps) in the multistep total synthesis of natural products.

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Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽

10.3390/sym13040720 ◽

2021 ◽

Vol 13 (4) ◽

pp. 720

Author(s):

Satomi Niwayama

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Functional Groups ◽

Organic Compounds ◽

Recent Progress ◽

Aqueous Media ◽

Building Blocks ◽

Organic Reactions ◽

Environmentally Benign ◽

Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

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