An efficient synthesis of 3-hetero-13,14-dihydro prostaglandin F1α analogues

被引：11

作者：

Gu, JX

Dirr, MJ

Wang, YL

Soper, DL

De, B

Wos, JA

Johnson, CR ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

[2] Procter & Gamble Co, Pharmaceut, Mason, OH 45040 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol015613a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new class of 3-hetero-13,14-dihydro prostaglandin F-1 alpha analogues was synthesized from a common intermediate. The latter was constructed via a two-step, three-component process. The lower chain, containing the 15-(phenoxymethyl) group, was synthesized in enantiopure form using Jacobsen's (salen)Co-catalyzed kinetic resolution of a terminal epoxide with phenol.

引用

页码：791 / 794

页数：4

共 16 条

[1] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE
BAILEY, WF
PUNZALAN, ER
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5404 - 5406
[2] COLEMAN RA, 1994, PHARMACOL REV, V46, P205
[3] STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL)
COREY, EJ
WEINSHENKER, NM
SCHAAF, TK
HUBER, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) : 5675 - +
[4] RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE
FELIX, AM
HEIMER, EP
LAMBROS, TJ
TZOUGRAKI, C
MEIENHOFER, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) : 4194 - 4196
[5] Novel and flexible entries into prostaglandins and analogues based on ring closing alkyne metathesis or alkyne cross metathesis
Fürstner, A
Grela, K
Mathes, C
Lehmann, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 11799 - 11805
[6] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P1234, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1234::AID-ANIE1234>3.0.CO
[7] 2-V
[8] A 2-STEP, 3-COMPONENT SYNTHESIS OF PGE(1) - UTILIZATION OF ALPHA-IODOENONES IN PD(0)-CATALYZED CROSS-COUPLINGS OF ORGANOBORANES
JOHNSON, CR
BRAUN, MP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) : 11014 - 11015
[9] 2-THIENYL(CYANO)COPPER LITHIUM - A LOWER ORDER, STABLE CUPRATE IN A BOTTLE PRECURSOR TO HIGHER-ORDER REAGENTS
LIPSHUTZ, BH
KOERNER, M
PARKER, DA
[J]. TETRAHEDRON LETTERS, 1987, 28 (09) : 945 - 948
[10] CLEAN AND CONVENIENT PROCEDURE FOR CONVERTING PRIMARY ALKYL IODIDES AND ALPHA,OMEGA-DIIODOALKANES INTO THE CORRESPONDING ALKYLLITHIUM DERIVATIVES BY TREATMENT WITH TERT-BUTYLLITHIUM
NEGISHI, E
SWANSON, DR
ROUSSET, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5406 - 5409

← 1 2 →