Practical and efficient 1 alpha-hydroxylation of 4,4-dimethyl-2-ene derivatives in terpenic series.

被引：13

作者：

Aranda, G

BertranneDelahaye, M

Azerad, R

Maurs, M

Cortes, M

Ramirez, H

Vernal, G

Prange, T

机构：

[1] UNIV PARIS 06,CHIM & BIOCHIM PHARMACOL & TOXICOL LAB,F-75006 PARIS,FRANCE

[2] PONTIFICIA UNIV CATOLICA CHILE,FAC QUIM,SANTIAGO,CHILE

[3] URA 1430,F-93017 BOBIGNY,FRANCE

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 01期

关键词：

D O I：

10.1080/00397919708004804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The third part of a triptycal synthesis providing 1 alpha-hydroxy compounds, through microbial hydroxylation in position-3 of terpenoid substrates, followed by dehydration to 4,4-dimethyl-2-ene compounds and subsequent allylic hydroxylation by SeO2/pyridine N-oxide, is described.

引用

页码：45 / 60

页数：16

共 42 条

[21] MODELS OF RETINOID METABOLISM - MICROBIAL BIOTRANSFORMATION OF ALPHA-IONONE AND BETA-IONONE
HARTMAN, DA
PONTONES, ME
KLOSS, VF
CURLEY, RW
ROBERTSON, LW
[J]. JOURNAL OF NATURAL PRODUCTS, 1988, 51 (05): : 947 - 953
[22] STUDIES IN THE POLYENE SERIES .37. PREPARATION OF 3-DEHYDRO-BETA-IONONE AND SOME 3-SUBSTITUTED BETA-IONONES
HENBEST, HB
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1951, (APR): : 1074 - 1078
[23] Chemistry of larixol I - Degradation of the side-chain and microbial hydroxylation
Herlem, D
Ouazzani, J
KhuongHuu, F
[J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1241 - 1244
[24] THE DIELS-ALDER ROUTE TO DRIMANE RELATED SESQUITERPENES - SYNTHESIS OF CINNAMOLIDE, POLYGODIAL, ISODRIMENINOL, DRIMENIN AND WARBURGANAL
HOLLINSHEAD, DM
HOWELL, SC
LEY, SV
MAHON, M
RATCLIFFE, NM
WORTHINGTON, PA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07): : 1579 - 1586
[25] PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .10. BIOCHEMICAL PREPARATION OF OPTICALLY-ACTIVE 4-HYDROXY-BETA-IONONE AND ITS TRANSFORMATION TO (S)-6-HYDROXY-ALPHA-IONONE
KAKEYA, H
SUGAI, T
OHTA, H
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (07): : 1873 - 1876
[26] KIEGIEL J, 1991, TETRAHEDRON LETT, V32, P6057, DOI 10.1016/0040-4039(91)80752-R
[27] HYDROXYLATION AND GLUCOSIDE CONJUGATION IN THE MICROBIAL-METABOLISM OF THE DITERPENE SCLAREOL
KOUZI, SA
MCCHESNEY, JD
[J]. XENOBIOTICA, 1991, 21 (10) : 1311 - 1323
[28] MICROBIAL-METABOLISM OF THE DITERPENE SCLAREOL - OXIDATION OF THE A RING BY SEPTOMYXA-AFFINIS
KOUZI, SA
MCCHESNEY, JD
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (08) : 2157 - 2164
[29] MICROBIAL MODELS OF MAMMALIAN METABOLISM - FUNGAL METABOLISM OF THE DITERPENE SCLAREOL BY CUNNINGHAMELLA SPECIES
KOUZI, SA
MCCHESNEY, JD
[J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02): : 483 - 490
[30] FERMENTATION OF FRAGRANCES - BIOTRANSFORMATION OF BETA-IONONE BY LASIODIPLODIA-THEOBROMAE
KRASNOBAJEW, V
HELMLINGER, D
[J]. HELVETICA CHIMICA ACTA, 1982, 65 (05) : 1590 - 1601

← 1 2 3 4 5 →