Construction of arene-fused-piperidine motifs by asymmetric addition of 2-trityloxymethylaryllithiums to nitroalkenes: The asymmetric synthesis of a dopamine D1 full agonist, A-86929

被引：53

作者：

Yamashita, M ^{[1
]}

Yamada, KI ^{[1
]}

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 07期

关键词：

D O I：

10.1021/ja031760n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process was highlighted by the first asymmetric synthesis of a dopamine D1 full agonist, A-86929. Copyright © 2004 American Chemical Society.

引用

页码：1954 / 1955

页数：2

共 34 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[2] The first asymmetric synthesis of a dopamine D1 agonist, dihydrexidine, employing asymmetric conjugate addition technology [J].

Asano, Y ;

Yamashita, M ;

Nagai, K ;

Kuriyama, M ;

Yamada, K ;

Tomioka, K .

TETRAHEDRON LETTERS, 2001, 42 (48) :8493-8495

[3] TRANS-10,11-DIHYDROXY-5,6,6A,7,8,12B-HEXAHYDROBENZO[A]PHENANTHRIDINE - A HIGHLY POTENT SELECTIVE DOPAMINE-D1 FULL AGONIST [J].

BREWSTER, WK ;

NICHOLS, DE ;

RIGGS, RM ;

MOTTOLA, DM ;

LOVENBERG, TW ;

LEWIS, MH ;

MAILMAN, RB .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1756-1764

[4] Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].

Doi, H ;

Sakai, T ;

Iguchi, M ;

Yamada, K ;

Tomioka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887

[5] Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols [J].

Duursma, A ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3700-3701

[6] An efficient enantioselective synthesis of the D1 agonist (5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopenta[c] phenanthrene-9,10-diol (A-86929) [J].

Ehrlich, PP ;

Ralston, JW ;

Michaelides, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2782-2785

[7]

Giardina WJ, 2001, CNS DRUG REV, V7, P305

[8] AMARYLLIDACEAE ALKALOIDS [J].

GRUNDON, MF .

NATURAL PRODUCT REPORTS, 1989, 6 (01) :79-84

[9] Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes [J].

Hayashi, T ;

Senda, T ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10716-10717

[10]

Hayashi T, 2001, SYNLETT, P879

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