Stereoselective synthesis of substituted γ-butyrolactones by the [3+2] annulation of allylic silanes with chlorosulfonyl isocyanate:: Enantioselective total synthesis of (+)-blastmycinone

被引：64

作者：

Peng, ZH ^{[1
]}

Woerpel, KA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol0069960

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A stereoselective synthesis of gamma -butyrolactones by the [3 + 2] annulation of allylic silanes with N-chlorosulfonyl isocyanate (CSI) was developed. An enantioselective total synthesis of (+)-blastmycinone was accomplished using this annulation as the key step.

引用

收藏

页码：675 / 678

页数：4

相关论文

共 35 条

[1] STEREOSELECTIVE CONSTRUCTION OF TETRAHYDROFURAN BY TIN-(IV)-CHLORIDE PROMOTED [3+2]-CYCLOADDITION OF ALLYLSILANE TO ALPHA-KETO ESTER [J].

AKIYAMA, T ;

ISHIKAWA, K ;

OZAKI, S .

CHEMISTRY LETTERS, 1994, (03) :627-630

[2]

BARENDS RJP, 1970, TETRAHEDRON LETT, V12, P5301

[3] Tritylallyldimethylsilane-TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols [J].

Brengel, GP ;

Meyers, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3230-3231

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .39. A FACILE SYNTHESIS OF GAMMA-SUBSTITUTED-GAMMA-BUTYROLACTONES IN EXCEPTIONALLY HIGH ENANTIOMERIC PURITY [J].

BROWN, HC ;

KULKARNI, SV ;

RACHERLA, US .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :365-369

[5] Ruthenium carbonyl-catalyzed [2+2+1]-cycloaddition of ketones, olefins, and carbon monoxide, leading to functionalized γ-butyrolactones [J].

Chatani, N ;

Tobisu, M ;

Asaumi, T ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7160-7161

[6] Total synthesis of (+)-blastmycinone, (-)-litsenolide C1, and related natural trisubstituted lactones via alkynyltungsten compounds [J].

Chen, MJ ;

Lo, CY ;

Chin, CC ;

Liu, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6362-6367

[7]

Connolly J. D., 1991, DICT TERPENOIDS, V1, P476

[8] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[9] 5-MEMBERED RING ANNULATION VIA PROPARGYLSILANES AND ALLYLSILANES [J].

DANHEISER, RL ;

DIXON, BR ;

GLEASON, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6094-6097

[10]

DUNKELBLUM E, 1972, TETRAHEDRON LETT, V14, P1551

← 1 2 3 4 →