Total synthesis of (+)-asperlin

被引：16

作者：

Akaike, Hideaki ^{[1
]}

Horie, Hidekazu ^{[1
]}

Kato, Keisuke ^{[1
]}

Akita, Hiroyuki ^{[1
]}

机构：

[1] Toho Univ, Fac Pharmaceut Sci, Chiba 2748510, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 09期

关键词：

D O I：

10.1016/j.tetasy.2008.04.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.

引用

页码：1100 / 1105

页数：6

共 23 条

[1] FORMAL TOTAL SYNTHESIS OF (-)-INDOLMYCIN [J].

AKITA, H ;

KAWAGUCHI, T ;

ENOKI, Y ;

OISHI, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) :323-328

[2]

ARGOUDEL.AD, 1966, TETRAHEDRON LETT, P1969

[3] ABSOLUTE-CONFIGURATIONS OF ASPERLIN, A METABOLITE OF ASPERGILLUS-NIDULANS, AND ITS RELATED COMPOUNDS [J].

FUKUYAMA, K ;

KATSUBE, Y ;

NODA, A ;

HAMASAKI, T ;

HATSUDA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (11) :3175-3181

[4] A novel entry to naturally occurring 5-alkenyl alpha,beta-unsaturated delta-lactones from D-glucose: syntheses of (+)-acetylphomalactone and (+)-asperlin [J].

Gomez, AM ;

deUralde, BL ;

Valverde, S ;

Lopez, JC .

CHEMICAL COMMUNICATIONS, 1997, (17) :1647-1648

[5]

Grubbs R.H., 2003, HDB METATHESIS, V3

[6] STEREOCONTROLLED SYNTHESIS OF (+/-)-ASPERLIN AND RELATED STEREOISOMERS USING ORGANOTITANIUM REAGENT [J].

HIRAOKA, H ;

FURUTA, K ;

IKEDA, N ;

YAMAMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2777-2780

[7] CONCISE ENANTIOSELECTIVE SYNTHESIS OF (+)-ASPERLIN BY APPLICATION OF THE SHARPLESS KINETIC RESOLUTION TO 2-FURYLMETHANOL DERIVATIVES BEARING ALKENYL MOIETY ON THE SIDE-CHAIN [J].

HONDA, T ;

SANO, N ;

KANAI, K .

HETEROCYCLES, 1995, 41 (03) :425-429

[8] Studies on the Sharpless asymmetric epoxidation of unsymmetrical divinylmethanols [J].

Honda, T ;

Mizutani, H ;

Kanai, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1729-1739

[9]

Kanai K, 1999, HETEROCYCLES, V50, P433

[10] New total synthesis of (±)-, (-) and (+)-chuangxinmycins [J].

Kato, K ;

Ono, M ;

Akita, H .

TETRAHEDRON, 2001, 57 (51) :10055-10062

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