USE OF DIHYDROQUINIDINE 9-O-(9'-PHENANTHRYL) ETHER IN OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION IN THE SYNTHESIS OF BRASSINOSTEROIDS

被引：32

作者：

BROSA, C

PERACAULA, R

PUIG, R

VENTURA, M

机构：

[1] Department of Organic Chemistry, C.E.T.S. Institut Químic de Sarrià

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 46期

关键词：

BRASSINOSTEROIDS; PLANT HORMONES; OSMIUM TETROXIDE; ASYMMETRIC DIHYDROXYLATION; DIHYDROQUINIDINE-9-O-(9'-PHENANTHRYL) ETHER;

D O I：

10.1016/S0040-4039(00)60932-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 22R,23R-homobrassinosteroid analogs are obtained in good yield from the corresponding precursor with a 22E-double bond by osmium-catalyzed asymmetric dihydroxylation using dihydroquinidine 9-O-(9'-phenantryl) ether (DHQD PHN) as chiral agent.

引用

页码：7057 / 7060

页数：4

共 8 条

[1] ABURATANI M, 1987, SYNTHESIS-STUTTGART, P181
[2] FURTHER INVESTIGATIONS OF THE STEREOCHEMISTRY OF ELECTROPHILIC ADDITION-REACTIONS OF THE STEROIDAL C-22 DOUBLE-BOND
HIRANO, Y
TAKATSUTO, S
IKEKAWA, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1775 - 1779
[3] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS
JACOBSEN, EN
MARKO, I
MUNGALL, WS
SCHRODER, G
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) : 1968 - 1970
[4] MARQUARDT V, 1991, RECENT ADV BRASSINOS, V7, P103
[5] NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS
SHARPLESS, KB
AMBERG, W
BELLER, M
CHEN, H
HARTUNG, J
KAWANAMI, Y
LUBBEN, D
MANOURY, E
OGINO, Y
SHIBATA, T
UKITA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) : 4585 - 4588
[6] TAKATSUTO S, 1982, CHEM PHARM BULL, V30, P4181
[7] STUDIES ON STEROIDAL PLANT-GROWTH REGULATOR .21. A STEREOSELECTIVE CONSTRUCTION OF BRASSINOSTEROID SIDE-CHAIN - A NEW PRACTICAL SYNTHESIS OF BRASSINOLIDE AND ITS ANALOGS
ZHOU, WS
HUANG, LF
SUN, LQ
PAN, XF
[J]. TETRAHEDRON LETTERS, 1991, 32 (46) : 6745 - 6748
[8] ZHOU WS, 1991, TETRAHEDRON-ASYMMETR, V2, P973

← 1 →