PHOTOINDUCED MOLECULAR-TRANSFORMATION .125. A NEW STEREOSELECTIVE AND REGIOSELECTIVE SYNTHESIS OF (+/-)-SESAMIN INVOLVING A BETA-SCISSION OF ALKOXYL RADICALS AS THE KEY STEP

被引：29

作者：

ORITO, K ^{[1
]}

YORITA, K ^{[1
]}

SUGINOME, H ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DIV ORGAN SYNTH,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)79448-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new stereo- and regioselective synthesis of (+/-)-sesamin (a representative lignan) based on our general method for the transformation of a cyclopentanone ring into a tetrahydrofuran ring involving a regioselective beta-scission of the alkoxyl radicals is reported.

引用

页码：5999 / 6002

页数：4

共 25 条

[1] BAHTNAGAR SP, 1977, J ORG CHEM, V18, P3089
[2] BECKER ED, 1962, TETRAHEDRON LETT, P157
[3] THE SYNTHESIS OF DL-SESAMIN AND DL-ASARININ
BEROZA, M
SCHECHTER, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (06) : 1242 - 1247
[4] Bertram SH, 1928, BIOCHEM Z, V197, P1
[5] REACTION OF DIMETHYL SODIO-3-KETOGLUTARATE WITH GLYOXAL AND SUBSTITUTED GLYOXALS - 1ST EXPEDITIOUS PREPARATION OF BICYCLO[3.3.0]OCTANE-3,7-DIONE - 5,7-DIHYDROXY-4-METHOXYCARBONYL-3-PHENYL-1-INDANONE
BERTZ, SH
RIHS, G
WOODWARD, RB
[J]. TETRAHEDRON, 1982, 38 (01) : 63 - 70
[6] Cohen WD, 1938, RECL TRAV CHIM PAY-B, V57, P653
[7] SYNTHESE DES DL-SESAMINS
FREUDENBERG, K
FISCHER, E
[J]. NATURWISSENSCHAFTEN, 1956, 43 (01) : 16 - 16
[8] DIE ABSOLUTE KONFIGURATION DER GRUPPE DES SESAMINS UND PINORESINOLS
FREUDENBERG, K
SIDHU, GS
[J]. CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (04): : 851 - 862
[9] FREUDENBERG K, 1956, BER, V89, P1230
[10] VESICANT PRINCIPLES OF POISON IVY AND RELATED PLANTS - SYNTHESIS OF THE URUSHIOLS, 1,2-DIHYDROXY-3-[(Z)-PENTADEC-8-ENYL]BENZENE AND 1,2-DIHYDROXY-3-PENTADECYLBENZENE
HALIM, H
LOCKSLEY, HD
MEMON, JJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (11): : 2331 - 2337

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