A GENERAL-APPROACH TO GAMMA-LACTONES VIA OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - SYNTHESIS OF (-)-MURICATACIN AND (+)-MURICATACIN

被引：138

作者：

WANG, ZM

ZHANG, XL

SHARPLESS, KB

SINHA, SC

SINHABAGCHI, A

KEINAN, E

机构：

[1] Scripps Res Inst, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA

[2] SCRIPPS RES INST, DEPT MOLEC BIOL, LA JOLLA, CA 92037 USA

[3] TECHNION ISRAEL INST TECHNOL, DEPT CHEM, IL-32000 HAIFA, ISRAEL

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)79001-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of hydroxy gamma-lactones have been prepared highly enantioselectively (92-99% ee) using either AD-mix-beta or AD-mix-alpha with both beta,gamma- and gamma,delta-unsaturated esters. The method is exemplified by the three-step synthesis of (-) and (+)- muricatacin in 74% yield and >99% ee.

引用

收藏

页码：6407 / 6410

页数：4

相关论文

共 27 条

[1] HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE [J].

ASKIN, D ;

WALLACE, MA ;

VACCA, JP ;

REAMER, RA ;

VOLANTE, RP ;

SHINKAI, I .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2771-2773

[2] AVENACIOLIDE, AN ANTIFUNGAL LACTONE FROM ASPERGILLUS AVENACEUS [J].

BROOKES, D ;

TIDD, BK ;

TURNER, WB .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (NOV) :5385-&

[3] STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR [J].

CHAKRABORTY, TK ;

GANGAKHEDKAR, KK .

TETRAHEDRON LETTERS, 1991, 32 (16) :1897-1898

[4] THE ENANTIOSPECIFIC SYNTHESIS OF (4S,5R)-4,5-DIHYDROXYDECANOIC AND (4S,5S)-4,5-DIHYDROXYDECANOIC ACID GAMMA-LACTONES, PROPOSED AUTOREGULATORS FROM STREPTOMYCES-GRISEUS [J].

COOPER, RD ;

JIGAJINNI, VB ;

WIGHTMAN, RH .

TETRAHEDRON LETTERS, 1984, 25 (45) :5215-5218

[5] 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-&

[6] STEREOSPECIFIC SYNTHESIS OF (+)-MURICATACIN - A BIOLOGICALLY-ACTIVE ACETOGENIN DERIVATIVE [J].

FIGADERE, B ;

HARMANGE, JC ;

LAURENS, A ;

CAVE, A .

TETRAHEDRON LETTERS, 1991, 32 (51) :7539-7542

[7]

GANTE J, 1991, CHEM ZTG, V115, P215

[8]

Gasey M., 1992, TETRAHEDRON LETT, V33, P965

[9] AN EFFICIENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES - THE CORE UNIT OF POTENT HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

MCKEE, SP ;

THOMPSON, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6500-6503

[10]

GRAFE U, 1982, J ANTIBIOT, V35, P609