Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction

被引：11

作者：

Yamauchi, S ^{[1
]}

Takeda, K ^{[1
]}

Ganaha, M ^{[1
]}

Kinoshita, Y ^{[1
]}

机构：

[1] Ehime Univ, Coll Agr, Matsuyama, Ehime 7908566, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 19期

关键词：

D O I：

10.1039/b206843p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel yeast reduction which gave (1R, 2S)-hydroxy ester 10 and (1S, 5S)-lactone 11 from racemic ketoester 12 was discovered. After 10 and 11 were converted to lactone 15 and 17, enantiomeric excesses were determined as 99% and 95%, respectively. This novel yeast reduction was applied to synthetic study of metabolites of 5-oxo-ETE 1. (R)-6,7-Dihydro- 5-HETE lactone 5 and (S)-6,7-dihydro-5-HETE lactone 6 were synthesized from 15 and 17, respectively.

引用

页码：2156 / 2160

页数：5

共 50 条

[41] Synthesis and transformations of perfluoroalkyl-containing 6,7-dihydro-1H-indazol-4(5H)-ones oximes
T. S. Khlebnikova
Yu. A. Piven’
A. V. Baranovskii
F. A. Lakhvich
Russian Journal of Organic Chemistry, 2015, 51 : 650 - 656
[42] Diastereoselective synthesis of (5R,7R)- and (5R,7S)-5,7-dimethyl-6,7-dihydro-5H-dibenz[c,e]azepines
Saudan, LA
Bernardinelli, G
Kündig, EP
SYNLETT, 2000, (04) : 483 - 486
[43] Synthesis and crystal structure determination of 6,7-dihydro-2-methoxy-4-(substituted)-5H-benzo[6,7]cyclohepta[1,2-b]pyridine-3-carbonitrile
Moustafa, A. M.
Girgis, A. S.
CRYSTAL RESEARCH AND TECHNOLOGY, 2007, 42 (04) : 400 - 406
[44] SYNTHESIS AND CHIRALITY OF (5R,6R)-5,6-DIHYDRO-BETA,PSI-CAROTENE-5,6-DIOL, (5R,6R,6'R)-5,6-DIHYDRO-BETA,EPSILON-CAROTENE-5,6-DIOL, (5S,6R)-5,6-EPOXY-5,6-DIHYDRO-BETA,PSI-CAROTENE AND (5S,6R6'R)-5,6-EPOXY-5,6-DIHYDRO-BETA,EPSILON-CAROTENE
ESCHENMOSER, W
UEBELHART, P
EUGSTER, CH
HELVETICA CHIMICA ACTA, 1979, 62 (08) : 2534 - 2538
[45] High pressure assisted synthetic approach for novel 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline derivatives and their assessment as anticancer agents
Haider Behbehani
Fatemah A. Aryan
Kamal M. Dawood
Hamada Mohamed Ibrahim
Scientific Reports, 10
[46] High pressure assisted synthetic approach for novel 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline derivatives and their assessment as anticancer agents
Behbehani, Haider
Aryan, Fatemah A.
Dawood, Kamal M.
Ibrahim, Hamada Mohamed
SCIENTIFIC REPORTS, 2020, 10 (01)
[47] SYNTHESIS OF 7-SUBSTITUTED 6,7-DIHYDRO-5H-PYRROLO[3,4-B]PYRIDIN-5-ONES - REACTION OF 7-HYDROXY DERIVATIVES WITH NUCLEOPHILES
GOTO, T
UTSUNOMIYA, S
AIBA, H
HAYASAKA, H
ENDO, M
WATANABE, R
ISHIZAKI, T
SATO, R
SAITO, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (06) : 1901 - 1910
[48] A Novel And Facile Synthesis of 2-(Cyclohexylamino)6,7-Dihydro-3-Aryl Benzofuran-4(5h)-Ones By One-Pot Three -Component Reaction
Baghernejad, Bita
Hekmatshoar, Rahim
Heravi, Majid M.
GAZI UNIVERSITY JOURNAL OF SCIENCE, 2010, 23 (04): : 429 - 433
[49] Synthesis and biological evaluation of novel 6,7-dihydro-5H-cyclopenta[d]pyrimidine and 5,6,7,8-tetrahydroquinazoline derivatives as sigma-1 (σ1) receptor antagonists for the treatment of pain
Lan, Yu
Songyang, Yiyan
Zhang, Lingli
Peng, Yan
Song, Jinchun
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (08) : 2051 - 2056
[50] Post-Ugi carbocyclization/fragmentation sequence for the synthesis of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones
Tran Thi Thu Trang
Peshkov, Anatoly A.
Jacobs, Jeroen
Van Meervelt, Luc
Peshkov, Vsevolod A.
Van der Eycken, Erik V.
TETRAHEDRON LETTERS, 2015, 56 (22) : 2882 - 2886

← 1 2 3 4 5 →