First total synthesis of natural 6-epiplakortolide E

被引：46

作者：

Jung, M ^{[1
]}

Ham, J ^{[1
]}

Song, J ^{[1
]}

机构：

[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026285x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Natural 6-epiplakortolide E was first synthesized from readily available 1-bromo-10-phenyldecane in 10 steps by using singlet oxygen-mediated Diels-Alder reaction to form cyclic peroxide followed by a directed iodolactonization to give the peroxylactone core.

引用

收藏

页码：2763 / 2765

页数：3

相关论文

共 22 条

[1] AN ANTIBODY-CATALYZED BIMOLECULAR DIELS-ALDER REACTION [J].

BRAISTED, AC ;

SCHULTZ, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7430-7431

[2] 4 NEW DIMERIC PEPTIDE ALKALOIDS, ANCHINOPEPTOLIDES-B-D, AND CYCLOANCHINOPEPTOLIDE-C, CONGENERS OF ANCHINOPEPTOLIDE-A, FROM THE MEDITERRANEAN MARINE SPONGE ANCHINOE-TENACIOR [J].

CASAPULLO, A ;

MINALE, L ;

ZOLLO, F ;

LAVAYRE, J .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1227-1233

[3]

CASTEEL DA, 1992, NAT PROD REP, P289

[4] Three new peroxides from the sponge Plakinastrella species [J].

Chen, Y ;

Killday, KB ;

McCarthy, PJ ;

Schimoler, R ;

Chilson, K ;

Selitrennikoff, C ;

Pomponi, SA ;

Wright, AE .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (02) :262-264

[5] PLAKORTOLIDE, A CYTOTOXIC PEROXYLACTONE FROM A PLAKORTIS SPONGE [J].

DAVIDSON, BS .

TETRAHEDRON LETTERS, 1991, 32 (49) :7167-7170

[6] Total synthesis of the alkoxydioxines (+)- and (-)-chondrillin and (+)- and (-)-plakorin via singlet oxygenation/radical rearrangement [J].

Dussault, PH ;

Eary, CT ;

Woller, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1789-1797

[7] ANTIBODY CATALYSIS OF A DIELS-ALDER REACTION [J].

HILVERT, D ;

HILL, KW ;

NARED, KD ;

AUDITOR, MTM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9261-9262

[8] SYNTHESIS AND ANTIMALARIAL ACTIVITY OF (+)-DEOXOARTEMISININ [J].

JUNG, M ;

LI, X ;

BUSTOS, DA ;

ELSOHLY, HN ;

MCCHESNEY, JD ;

MILHOUS, WK .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1516-1518

[9] A SHORT AND STEREOSPECIFIC SYNTHESIS OF (+)-DEOXOARTEMISININ AND (-)-DEOXODESOXYARTEMISININ [J].

JUNG, MK ;

LI, X ;

BUSTOS, DA ;

ELSOHLY, HN ;

MCCHESNEY, JD .

TETRAHEDRON LETTERS, 1989, 30 (44) :5973-5976

[10]

KAWASAKI L, 1994, J CHEM SOC CHEM COMM, V59, P6823