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

被引：63

作者：

Snider, BB ^{[1
]}

Zeng, HB ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 02期

关键词：

D O I：

10.1021/jo0264980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：545 / 563

页数：19

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