Enantiodivergent synthesis of either enantiomer of ABCDE-ring analogue of antitumor antibiotic fredericamycin A via intramolecular [4+2] cycloaddition approach

被引：29

作者：

Akai, S ^{[1
]}

Tsujino, T ^{[1
]}

Fukuda, N ^{[1
]}

Iio, K ^{[1
]}

Takeda, Y ^{[1
]}

Kawaguchi, KI ^{[1
]}

Naka, T ^{[1
]}

Higuchi, K ^{[1
]}

Kita, Y ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 25期

关键词：

D O I：

10.1021/ol016696y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochiral diol 2 using 1-ethoxyvinyl 2-furoate 3 led to the pivotal intermediate (R)-4.

引用

页码：4015 / 4018

页数：4

共 27 条

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