A short, enantiospecific synthesis of a protected seco acid precursor to (R,R)-(-)-pyrenophorin

被引：14

作者：

Hoffman, RV

Patonay, T

Nayyar, NK

Tao, JH

机构：

[1] Dept. of Chemistry and Biochemistry, New Mexico State University, Las Cruces

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 14期

关键词：

D O I：

10.1016/0040-4039(96)00323-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described herein is a four-step enantiospecific synthesis of a protected seco acid precursor of (R,R)-(-)-pyrenophorin in 23% yield from a chiral beta-ketoester 3, which can be prepared in one step from ethyl acetoacetate by a standard procedure. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：2381 / 2384

页数：4

相关论文

共 35 条

[11] A SHORT ROUTE TO PYRENOPHORIN AND VERMICULINE [J].

HASE, TA ;

OURILA, A ;

HOLMBERG, C .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) :3137-3139

[12] A SYNTHESIS OF (-)-PYRENOPHORIN USING 4-DMAP-CATALYZED ESTER EXCHANGE-REACTION OF PHOSPHONOACETATES WITH LACTOLS [J].

HATAKEYAMA, S ;

SATOH, K ;

SAKURAI, K ;

TAKANO, S .

TETRAHEDRON LETTERS, 1987, 28 (24) :2717-2720

[13] THE REACTIONS OF ALPHA-ARYLSULFONOXY KETONES WITH NUCLEOPHILES [J].

HOFFMAN, RV ;

JANKOWSKI, BC ;

CARR, CS ;

DUESLER, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (02) :130-135

[14] SYNTHETIC TRANSFORMATIONS USING ARENESULFONYLOXY GROUPS, 1ST AS ELECTROPHILES, THEN AS LEAVING GROUPS [J].

HOFFMAN, RV .

TETRAHEDRON, 1991, 47 (07) :1109-1135

[15] SYNTHESIS OF 2-[[(PARA-NITROPHENYL)SULFONYL]OXY] 3-KETO ESTERS FROM 3-KETO ESTERS AND (PARA-NITROPHENYL)SULFONYL PEROXIDE [J].

HOFFMAN, RV ;

WILSON, AL ;

KIM, HO .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1267-1270

[16] A SIMPLE SYNTHETIC APPROACH TO CBZ-PHE-PSI-(CH2)GLY-PRO-OME AND RELATED PEPTIDE ISOSTERES [J].

HOFFMAN, RV ;

KIM, HO .

TETRAHEDRON LETTERS, 1992, 33 (25) :3579-3582

[17] 2-[[(P-NITROPHENYL)SULFONYL]OXY] 3-KETO ESTERS AS INTERMEDIATES FOR THE REGIOSPECIFIC PREPARATION OF 2-[[(P-NITROPHENYL)SULFONYL]OXY] KETONES [J].

HOFFMAN, RV ;

KIM, HO ;

LEE, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1933-1936

[18] SYNTHESIS OF A PYRENOPHORIN PRECURSOR, 7-HYDROXY-4-OXO-2-OCTENOIC ACID BY THE DIRECT PALLADIUM CATALYZED COUPLING OF AN ACRYLIC TIN REAGENT WITH AN ACID CHLORIDE [J].

LABADIE, JW ;

STILLE, JK .

TETRAHEDRON LETTERS, 1983, 24 (40) :4283-4286

[19]

LEFLOCH Y, 1995, B SOC CHIM FR, V132, P114

[20] STEREOSELECTIVE SYNTHESIS OF (+/-)-METHYL NONACTATE AND (+/-)-METHYL 8-EPI-NONACTATE [J].

LYGO, B ;

OCONNOR, N .

TETRAHEDRON LETTERS, 1987, 28 (31) :3597-3600

← 1 2 3 4 →