Total synthesis of (-)-reveromycin B

被引：23

作者：

Cuzzupe, AN ^{[1
]}

Hutton, CA ^{[1
]}

Lilly, MJ ^{[1
]}

Mann, RK ^{[1
]}

Rizzacasa, MA ^{[1
]}

Zammit, SC ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3052, Australia

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991281m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) is described. A novel, convergent, and stereoselective reaction sequence was utilized to construct the 5,6-spiroketal system 10 which was converted into the natural product 2 by a 16-step sequence.

引用

页码：191 / 194

页数：4

共 28 条

[1]

[Anonymous], 1997, ORGANIC REACTIONS

[2] EINE PARTIALSYNTHESE DES 'ALL'-TRANS-METHYL-BIXINS UND DES 'ALL'-TRANS-4.4'-DESDIMETHYL-METHYL-BIXINS [J].

BUCHTA, E ;

ANDREE, F .

CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (12) :3111-3116

[3] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[4] Enantioselective total synthesis of reveromycin B [J].

Drouet, KE ;

Theodorakis, EA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :456-457

[5] TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453

[6] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[7] CATALYTIC, ASYMMETRIC-SYNTHESIS OF THE CARBACEPHEM FRAMEWORK [J].

GUZZO, PR ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4862-4867

[8] ENANTIOMERICALLY PURE SYNTHETIC BUILDING-BLOCKS WITH 4 C-ATOMS AND 2 OR 3 FUNCTIONAL-GROUPS FROM BETA-HYDROXY-BUTANOIC, MALIC, AND TARTARIC ACID [J].

HUNGERBUHLER, E ;

SEEBACH, D ;

WASMUTH, D .

HELVETICA CHIMICA ACTA, 1981, 64 (05) :1467-1487

[9] PHEROMONE SYNTHESES - MODEL REACTIONS FOR THE SYNTHESIS OF POLYETHER ANTIBIOTICS [J].

IRELAND, RE ;

HABICH, D .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1418-1427

[10] REVEROMYCINS, NEW INHIBITORS OF EUKARYOTIC CELL-GROWTH .3. STRUCTURES OF REVEROMYCIN-A, REVEROMYCIN-B, REVEROMYCIN-C AND REVEROMYCIN-D [J].

KOSHINO, H ;

TAKAHASHI, H ;

OSADA, H ;

ISONO, K .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1420-1427

← 1 2 3 →