Asymmetric synthesis of the balanol heterocycle via a palladium-mediated epimerization and olefin metathesis

被引：64

作者：

Cook, GR ^{[1
]}

Shanker, PS ^{[1
]}

Peterson, SL ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 04期

关键词：

D O I：

10.1021/ol990705+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The enantioselective formal synthesis of balanol, a potent protein kinase C inhibitor, was accomplished from D-serine utilizing a Pd-catalyzed equilibration of diastereomeric 5-vinyloxazolines to set the stereochemistry of the vicinal amino and hydroxyl groups. A ruthenium-catalyzed ring closing metathesis was employed to form the seven-membered nitrogen heterocyle.

引用

收藏

页码：615 / 617

页数：3

相关论文

共 40 条

[1] TOTAL SYNTHESIS OF BALANOL - A POTENT PROTEIN-KINASE-C INHIBITOR OF FUNGAL ORIGIN [J].

ADAMS, CP ;

FAIRWAY, SM ;

HARDY, CJ ;

HIBBS, DE ;

HURSTHOUSE, MB ;

MORLEY, AD ;

SHARP, BW ;

VICKER, N ;

WARNER, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2355-2362

[2] A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo[2.2.1]heptane ring systems from D(-)-quinic acid: Application to the formal syntheses of (-)-balanol and (-)-epibatidine [J].

Albertini, E ;

Barco, A ;

Benetti, S ;

DeRisi, C ;

Pollini, GP ;

Zanirato, V .

TETRAHEDRON, 1997, 53 (50) :17177-17194

[3] Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B [J].

Angle, SR ;

Henry, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8549-8552

[4]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[5] COMPARISON OF BALANOL FROM VERTICILLIUM BALANOIDES AND OPHIOCORDIN FROM CORDYCEPS OPHIOGLOSSOIDES [J].

BOROS, C ;

HAMILTON, SM ;

KATZ, B ;

KULANTHAIVEL, P .

JOURNAL OF ANTIBIOTICS, 1994, 47 (09) :1010-1016

[6] Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid [J].

Cook, GR ;

Shanker, PS .

TETRAHEDRON LETTERS, 1998, 39 (21) :3405-3408

[7] An efficient synthesis of (2S,3R)-3-hydroxylysine via ruthenium catalyzed asymmetric hydrogenation [J].

Coulon, E ;

Cristina, M ;

de Andrade, C ;

Ratovelomanana-Vidal, V ;

Genêt, JP .

TETRAHEDRON LETTERS, 1998, 39 (36) :6467-6470

[8] Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A [J].

Defauw, JM ;

Murphy, MM ;

Jagdmann, GE ;

Hu, H ;

Lampe, JW ;

Hollinshead, SP ;

Mitchell, TJ ;

Crane, HM ;

Heerding, JM ;

Mendoza, JS ;

Davis, JE ;

Darges, JW ;

Hubbard, FR ;

Hall, SE .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5215-5227

[9] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[10] PROTEIN-KINASE-C INHIBITORY ACTIVITIES OF BALANOL ANALOGS BEARING CARBOXYLIC-ACID REPLACEMENTS [J].

HEERDING, JM ;

LAMPE, JW ;

DARGES, JW ;

STAMPER, ML .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) :1839-1842

← 1 2 3 4 →