Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

Barry B Snider; Hongbo Zeng

doi:10.1021/jo0264980

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Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

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Peer reviewed

Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

Barry B Snider and Hongbo Zeng

Journal of Organic Chemistry, Vol.68(2), pp.545-563

01/01/2003

DOI: https://doi.org/10.1021/jo0264980

PMID: 12530882

Abstract

Quinazolines - chemical synthesis

Cyclization

Oxidation-Reduction

Stereoisomerism

Indoles - chemical synthesis

Models, Molecular

Indicators and Reagents

Molecular Structure

Catalysis

Chemical Synthesis

Organic Chemistry

The first syntheses of (-)-fumiquinazolines A, B, and I, which proceed in 14 steps from protected tryptophan, anthranilic acid, leucine, and alanine in 7% overall yield, are described. Tricycle 30 was formed by a palladium-catalyzed cyclization. Oxidation of 30a with saccharine-derived oxaziridine 21 for fumiquinazolines A and B and oxidation of 30b with dimethyldioxirane for fumiquinazoline I selectively formed the appropriate imidazoindolone stereoisomers. Application of the Ganesan-Mazurkiewicz cyclization completed the syntheses. Efficient 14-step syntheses of (-)-fumiquinazolines C (7) and E (3) and a 15-step synthesis of (-)-fumiquinazoline H (8) using FmocNHCH(CH2SePh)CO2H as a dehydroalanine precursor that spontaneously eliminated benzeneselenol without oxidation under the cyclization conditions are also reported. Model 86 for fiscalins A with the H and OH anti to each other has been prepared, but the procedure that worked for the model failed with the fully functionalized side chain.

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Title: Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A
Creators: Barry B Snider (Author) - Department of Chemistry, MS015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Hongbo Zeng (Author)
Publication Details: Journal of Organic Chemistry, Vol.68(2), pp.545-563
Publisher: United States
Grant note: GM-50151 / NIGMS NIH HHS
Identifiers: 9923958133301921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

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