Improved procedure for the enantiometric synthesis of 1-hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicyclo[3.30]octane lignans: Total syntheses of(+)-paulownin, (+)-phrymarin I and (+)-phrymarin II

被引：10

作者：

Ishibashi, F ^{[1
]}

Hayashita, M

Okazaki, M

Shuto, Y

机构：

[1] Nagasaki Univ, Fac Fisheries, Nagasaki 8528521, Japan

[2] Ehime Univ, Fac Agr, Matsuyama, Ehime 790, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2001年 / 65卷 / 01期

关键词：

enantiomeric synthesis; (+)-paulownin; (+)-phrymarin I; (+)-phrymarin II; photocyclization;

D O I：

10.1271/bbb.65.29

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Short enantiomeric syntheses of the 1-hydroxy/acetoxy-3,7-dioxabicyclo[3.3.0]octane lignans, (+)-paulownin, and (+)-phrymarin I and II, were accomplished by starting from the chiral synthon, (R)-(+)-3-hydroxybutanolide, and employing photocyclization as the key step.

引用

页码：29 / 34

页数：6

共 15 条

[1] A TOTAL SYNTHESIS OF RACEMIC PAULOWNIN USING A TYPE-II PHOTOCYCLIZATION REACTION [J].

KRAUS, GA ;

CHEN, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3464-3466

[2] THE ANTIVIRAL ACTION OF LIGNANS [J].

MACRAE, WD ;

HUDSON, JB ;

TOWERS, GHN .

PLANTA MEDICA, 1989, (06) :531-535

[3] BIOLOGICAL-ACTIVITIES OF LIGNANS [J].

MACRAE, WD ;

TOWERS, GHN .

PHYTOCHEMISTRY, 1984, 23 (06) :1207-1220

[4] Total synthesis of (+)-paulownin [J].

Okazaki, M ;

Ishibashi, F ;

Shuto, Y ;

Taniguchi, E .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (04) :743-745

[5] Total synthesis of (+)-phrymarolin I from (+)-malic acid [J].

Okazaki, M ;

Ishibashi, F ;

Shuto, Y ;

Taniguchi, E .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (04) :660-663

[6] APPROACHES TO 2,6-DIARYL-3,7-DIOXABICYCLO[3.3.0]OCTANE LIGNANS VIA ASYMMETRIC-SYNTHESIS OF DIHYDROFURAN AND TETRAHYDROFURAN DERIVATIVES [J].

PELTER, A ;

WARD, RS ;

LITTLE, GM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10) :2775-2790

[7] COMBINATION OF BORANE-DIMETHYL SULFIDE COMPLEX WITH CATALYTIC SODIUM TETRAHYDROBORATE AS A SELECTIVE REDUCING AGENT FOR ALPHA-HYDROXY ESTERS, VERSATILE CHIRAL BUILDING BLOCK FROM (S)-(-)-MALIC ACID [J].

SAITO, S ;

HASEGAWA, T ;

INABA, M ;

NISHIDA, R ;

FUJII, T ;

NOMIZU, S ;

MORIWAKE, T .

CHEMISTRY LETTERS, 1984, (08) :1389-1392

[8]

TAKAHASHI K, 1966, CHEM PHARM BULL, V14, P641

[9]

TAKANO S, 1989, J CHEM SOC CHEM COMM, P189

[10] ENANTIOSELECTIVE SYNTHESIS OF NATURAL DIBENZYLBUTYROLACTONE LIGNANS (-)-ENTEROLACTONE, (-)-HINOKININ, (-)-PLUVIATOLIDE, (-)-ENTERODIOL, AND FUROFURAN LIGNAN (-)-EUDESMIN VIA TANDEM CONJUGATE ADDITION TO GAMMA-ALKOXYBUTENOLIDES [J].

VANOEVEREN, A ;

JANSEN, JFGA ;

FERINGA, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5999-6007

← 1 2 →