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Generation of Molecular Shape Diverstiy. From Privileged Scaffolds to Diverted Total Synthesis

100%

Dai W.-M.

Diversity Oriented Synthesis

2012

vol. 1

issue 1

Molecular shape is a presentation of a molecule’s three-dimensional structure and its volume of space and surface electrostatic potential map collectively define the function, e. g. as a modulator or probe to biological targets. Molecular shape diversity for compound libraries with multiple scaffolds (rich skeletal diversity) is recognized as a prerequisite for discovering broad bioactivity. Established strategies and methodologies for diversity-oriented synthesis (DOS) are useful for generating molecular shape diversity by synthesizing natural product-like compounds. On the other hand, diverted total synthesis (DTS) offers natural products and analogues with a higher degree of structural diversity and complexity. Examples of DOS of privileged heterocycles and DTS of amphidinolide T marine macrolides from the author’s laboratories are illustrated.

One-Pot Synthesis of Dibenz[b,f][1,4]oxazepines via Mg(ClO4)2-Catalyzed Ugi Four-Component Reaction and Microwave-Assisted Intramolecular SNAr

51%

Luo J., Wu J., Dai W.-M.

Diversity Oriented Synthesis

2012

vol. 1

issue 1

A general one-pot synthesis of dibenz[b,f][1,4] oxazepine-11(10H)-carboxamides is described. The Ugi four-component reaction (U-4CR) of 2-aminophenols, cyclohexyl isocyanide, 2-chloro-5-nitrobenzaldehyde, and 2-bromobenzoic acids in MeOH in the presence of 25 mol% Mg(ClO4)2 at 30-40 .C for 22-95 h gave the linear Ugi products. The latter were treated with aqueous K2CO3 in MeOH under microwave heating at 120 .C for 10 min for promoting the intramolecular nucleophilic aromatic substitution (SNAr), affording the 6/7/6-fused tricyclic heterocycles in 61-85% yields.

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2 Diversity Oriented Synthesis

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2 Dai W.-M.

1 Luo J.

1 Wu J.

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Generation of Molecular Shape Diverstiy. From Privileged Scaffolds to Diverted Total Synthesis

One-Pot Synthesis of Dibenz[b,f][1,4]oxazepines via Mg(ClO4)2-Catalyzed Ugi Four-Component Reaction and Microwave-Assisted Intramolecular SNAr