TOTAL SYNTHESIS OF (-)-LAMINITOL (1D-4C-METHYL-MYO-INOSITOL) VIA MICROBIAL OXIDATION OF TOLUENE

被引：24

作者：

CARLESS, HAJ

OAK, OZ

机构：

[1] Department of Chemistry, Birkbeck College, Gordon House, London, WC1H 0PP

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)74301-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral cyclohexadienediol (4), available from oxidation of toluene by Pseudomonas putida, can be converted via selective epoxidation and ring-opening to the C-methyl conduritol F (8) and thence to (-)-laminitol (2).

引用

页码：1671 / 1674

页数：4

共 34 条

[1] ANDERSON L, 1972, CARBOHYDRATES A, V1, P519
[2] CYCLITOLS .35. TRIDENTATE COMPLEXING OF SOME C-METHYL-CYCLITOLS AND C-HYDROXYMETHYL-CYCLITOLS WITH BORATE IONS
ANGYAL, SJ
KLAVINS, JE
MILLS, JA
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (05) : 1075 - 1086
[3] IDENTIFICATION OF (1S)-PHOSPHORYLOXY-(2R,4S)-DIHYDROXYCYCLOHEXANE AS A POTENT INHIBITOR OF INOSITOL MONOPHOSPHATASE
BAKER, R
LEESON, PD
LIVERTON, NJ
KULAGOWSKI, JJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) : 462 - 464
[4] RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES
BILLINGTON, DC
[J]. CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) : 83 - 122
[5] TOTAL SYNTHESIS OF MYOINOSITOL POLYPHOSPHATES FROM BENZENE VIA CONDURITOL-B DERIVATIVES
CARLESS, HAJ
BUSIA, K
[J]. TETRAHEDRON LETTERS, 1990, 31 (24) : 3449 - 3452
[6] TOTAL SYNTHESIS OF CHIRO-INOSITOL 2,3,5-TRISPHOSPHATE - A MYOINOSITOL 1,4,5-TRISPHOSPHATE ANALOG FROM BENZENE VIA PHOTOOXIDATION
CARLESS, HAJ
BUSIA, K
[J]. TETRAHEDRON LETTERS, 1990, 31 (11) : 1617 - 1620
[7] PHOTOCHEMICAL ROUTES FROM ARENES TO INOSITOL INTERMEDIATES - THE PHOTO-OXIDATION OF SUBSTITUTED CIS-CYCLOHEXA-3,5-DIENE-1,2-DIOLS
CARLESS, HAJ
BILLINGE, JR
OAK, OZ
[J]. TETRAHEDRON LETTERS, 1989, 30 (23) : 3113 - 3116
[8] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE
CHA, JK
CHRIST, WJ
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 3943 - 3946
[9] CHA JK, 1983, TETRAHEDRON LETT, V24, P3947
[10] TOTAL SYNTHESIS OF THE 5-METHYLENEPHOSPHONATE ANALOG OF D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE
FALCK, JR
ABDALI, A
WITTENBERGER, SJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) : 953 - 955

← 1 2 3 4 →