2-nitrophenyl isocyanide as a versatile convertible isocyanide: rapid access to a fused gamma-lactam beta-lactone bicycle.

doi:10.1021/jo800486k

Paper

2-nitrophenyl isocyanide as a versatile convertible isocyanide: rapid access to a fused gamma-lactam beta-lactone bicycle.

Published May 7, 2008 · C. Gilley, Yoshihisa Kobayashi

The Journal of organic chemistry

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Abstract

2-Nitrophenyl isocyanide is introduced as a convertible isocyanide with demonstration of its feasibility and applicability in an efficient synthesis of the fused gamma-lactam beta-lactone bicycle of proteasome inhibitor omuralide. Starting from a linear keto acid precursor, the fused gamma-lactam beta-lactone bicycle was prepared in four steps by a sequential biscyclization strategy; a stereocontrolled Ugi reaction and the concomitant direct beta-lactonization following the formation of an N-acylbenzotriazole intermediate. The N-acylbenzotriazole is amenable to intra- or intermolecular attack from a variety of nucleophiles with a catalytic amount of base to form the pyroglutamic acid derivatives.

Study Snapshot

2-Nitrophenyl isocyanide is a versatile convertible isocyanide that efficiently synthesizes the fused gamma-lactam beta-lactone bicycle of proteasome inhibitor omuralide in four steps.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

2-nitrophenyl isocyanide as a versatile convertible isocyanide: rapid access to a fused gamma-lactam beta-lactone bicycle.

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References

Citations

Synthesis of triisocyanomesitylene β‑diketiminato copper(I) complexes and evaluation of isocyanide π-back bonding

The synthesized 2,4,6-triisocyanomesitylene ligand and 1,4-isocyanobenzene ligands create unique copper(I) complexes with enhanced -back bonding between copper(I) centers and isocyanide moieties.

Application of the Cleavable Isocyanide in Efficient Approach to Pyroglutamic Acid Analogues with Potential Biological Activity

The developed methods efficiently synthesize pyroglutamic acid analogues 28, 29, and 34, with potential biological activity, using 1-(2,2-dimethoxyethyl)-2-isocyanobenzene as a cleavable isocyanide and strong nucleophile.

Straightforward access to complex isoindolinones from the Ugi reaction of o-nitrobenzoic acid derivatives.

The Ugi reaction of 2-nitrobenzoic acid derivatives allows for the diverse synthesis of complex isoindolinones, which can be transformed into polycyclic fused isoindolinones via Pictet-Spengler cyclization or O-alkylation/metathesis sequence

A bicyclization reaction with two molecular allenyl ketones and isocyanides: synthesis of a lactone-containing azaspirocycle derivative.

This novel bicyclization reaction efficiently creates complex spirocyclic lactam-lactone systems with high synthetic efficiency, atom economy, and broad substrate scope under mild conditions.

Total Synthesis of TAN1251C via Diastereoselective Construction of the Azaspiro Skeleton.

Diastereoselective reduction of enamide 15 or oxime 23 allows for the efficient total synthesis of TAN1251C, a novel spiro-fused cyclohexanone with desired stereochemistry.