FORMAL TOTAL SYNTHESES OF (-)-ISOAVENACIOLIDE AND (-)-ETHISOLIDE FROM L-QUEBRACHITOL

被引：22

作者：

CHIDA, N ^{[1
]}

TOBE, T ^{[1
]}

SUWAMA, M ^{[1
]}

OHTSUKA, M ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT APPL CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 20期

关键词：

D O I：

10.1039/p19920002667

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective conversions of the naturally occurring optically active Cyclitol, L-quebrachitol 5, into the known synthetic intermediates, 3 and 4, for preparations of structurally interesting bislactones, (-)-isoavenaciolide 1 and (-)-ethisolide 2, respectively, are described. These bislactones, 3 and 4, were synthesized from the common intermediate 19, which was prepared by periodate oxidation of the bicyclic cyclitol derivative 17.

引用

页码：2667 / 2673

页数：7

共 45 条

[1] ANCHIMERICALLY ASSISTED DEMETHYLATION OF METHYL ETHERS IN INOSITOL DERIVATIVES WITH AN ALCL3-NAI SYSTEM
AKIYAMA, T
TAKECHI, N
SHIMA, H
OZAKI, S
[J]. CHEMISTRY LETTERS, 1990, (10) : 1881 - 1884
[2] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL
AKIYAMA, T
TAKECHI, N
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (10) : 1433 - 1434
[3] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES
AKIYAMA, T
NISHIMOTO, H
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1335 - 1338
[4] AKIYAMA T, 1991, SYNLETT, P831
[5] A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION
AKIYAMA, T
SHIMA, H
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5593 - 5596
[6] 2 NEW MOULD METABOLITES RELATED TO AVENACIOLIDE
ALDRIDGE, DC
TURNER, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (13): : 2431 - &
[7] SYNTHESIS OF BIS-GAMMA-LACTONES FROM DIACETONE GLUCOSE .4. OPTICALLY-ACTIVE AVENACIOLIDE AND ISOAVENACIOLIDE
ANDERSON, RC
FRASERREID, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) : 4781 - 4786
[8] ANGYAL SJ, 1963, METHODS CARBOHYDR CH, V2, P87
[9] TOTAL SYNTHESIS OF (+/-)-ISOAVENACIOLIDE AND (+/-)-AVENACIOLIDE
BURKE, SD
PACOFSKY, GJ
PISCOPIO, AD
[J]. TETRAHEDRON LETTERS, 1986, 27 (29) : 3345 - 3348
[10] SYNTHESIS OF ETHISOLIDE, ISOAVENACIOLIDE, AND AVENACIOLIDE
BURKE, SD
PACOFSKY, GJ
PISCOPIO, AD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2228 - 2235

← 1 2 3 4 5 →