SYNTHESIS OF PHORACANTHOLIDE-I BASED ON STEREOSPECIFIC FRAGMENTATION REACTIONS

被引：13

作者：

NAGUMO, S ^{[1
]}

SUEMUNE, H ^{[1
]}

SAKAI, K ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 40期

关键词：

R-(-)-PHORACANTHOLIDE-I; FRAGMENTATION; EPOXIDATION; HYDROGEN BOND; SILICA GEL; ACETAL;

D O I：

10.1016/0040-4039(91)80090-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phoracantholide I was synthesized on the basis of silica gel-catalyzed fragmentation to the ring-enlarged lactones.

引用

页码：5585 / 5588

页数：4

共 24 条

[1] ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].

DEOL, BS ;

RIDLEY, DD ;

SIMPSON, GW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2459-2467

[2]

ESCHENMOSER A, 1979, ANGEW CHEM INT EDIT, V18, P634

[3]

Fr?ter G., 1980, HELV CHIM ACTA, V63, P1383

[4]

FUCHS PL, 1979, J AM CHEM SOC, V101, P3567

[5] SYNTHESIS OF 2 NATURALLY OCCURRING 10-MEMBERED RING LACTONES - (+/-)-PHORACANTHOLIDE J AND I [J].

GERLACH, H ;

KUNZLER, P ;

OERTLE, K .

HELVETICA CHIMICA ACTA, 1978, 61 (04) :1226-1231

[6] MECHANISMS AND STEREOCHEMISTRY OF HETEROLYTIC FRAGMENTATION [J].

GROB, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :535-&

[7] THE SYNTHESIS OF MACRO-CYCLIC AND MEDIUM CYCLIC-COMPOUNDS .2. THE SYNTHESIS AND THE ABSOLUTE-CONFIGURATION OF PHORACANTHOLIDE-I AND PHORACANTHOLIDE-J - THE DEFENSIVE SECRETION OF THE EUCARYPT LONGICORN, PHORACANTHA-SYNONYMA [J].

KITAHARA, T ;

KOSEKI, K ;

MORI, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (02) :389-393

[8] COMPUTER-ASSISTED MECHANISTIC EVALUATION OF ORGANIC-REACTIONS .13. A GENERAL TREATMENT OF NUCLEOPHILIC CHEMISTRY [J].

METIVIER, P ;

GUSHURST, AJ ;

JORGENSEN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3724-3738

[9] NEW RING CONVERSION OF MONOCYCLIC KETONES TO BICYCLOENONE SKELETONS [J].

MIYAO, Y ;

TANAKA, M ;

SUEMUNE, H ;

SAKAI, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1535-1536

[10] CHEMISTRY OF METASTERNAL GLAND SECRETION OF EUCALYPT LONGICORN PHORACANTHA-SYNONYMA (COLEOPTERA-CERAMBYCIDAE) [J].

MOORE, BP ;

BROWN, WV .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (06) :1365-1374

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