Total synthesis of natural (+)-FR900482 .1. Synthetic and end-game strategies

被引：37

作者：

Katoh, T ^{[1
]}

Itoh, E ^{[1
]}

Yoshino, T ^{[1
]}

Terashima, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 20期

关键词：

D O I：

10.1016/0040-4039(96)00593-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic strategy for natural (+)-FR900482 (1) war developed by featuring a convergent and enantioselective sequence which commences with S-hydroxyisophthalic acid and L-diethyl tartrate. The proposed key intermediate 4 was synthesized starting from FK973, the triacetyl derivative of 1, and successful reconversion of 4 into 1 was also achieved. These preliminary studies definitely demonstrated that 4 is suitable as a potential relay compound toward 1 and that the crucial final sequence of reactions (4-->1) involving delicate deprotection and oxidation steps can be realized. Copyright (C) 1996 Elsevier Science Ltd

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页码：3471 / 3474

页数：4

相关论文

共 29 条

[1]

BAN Y, 1994, HETEROCYCLES, V39, P657

[2] ON MECHANISM OF SULFONAMIDE CLEAVAGE BY ARENE ANION RADICALS [J].

CLOSSON, WD ;

JI, S ;

SCHULENBERG, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :650-+

[3]

DANISHEFSKY SJ, 1995, SYNLETT, P475

[4] A NEW APPROACH TO THE BICYCLIC HYDROXYLAMINE HEMIKETAL RING-SYSTEM OF ANTITUMOR-ANTIBIOTIC FR900482 VIA OXIDATIVE RING EXPANSION OF A TETRAHYDROPYRROLO[1,2-A]INDOLE [J].

DMITRIENKO, GI ;

DENHART, D ;

MITHANI, S ;

PRASAD, GKB ;

TAYLOR, NJ .

TETRAHEDRON LETTERS, 1992, 33 (39) :5705-5708

[5] SYNTHETIC APPROACHES TOWARD FR-900482 .1. STEREOSELECTIVE SYNTHESIS OF A PENTACYCLIC MODEL-COMPOUND [J].

FUKUYAMA, T ;

GOTO, S .

TETRAHEDRON LETTERS, 1989, 30 (47) :6491-6494

[6] TOTAL SYNTHESIS OF (+/-)-FR-900482 [J].

FUKUYAMA, T ;

XU, LH ;

GOTO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :383-385

[7] TOTAL SYNTHESIS OF (+-)-FAWCETTIMINE [J].

HEATHCOCK, CH ;

BLUMENKOPF, TA ;

SMITH, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1548-1562

[8] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .4. HEMATOLOGICAL TOXICITY IN MICE [J].

HIRAI, O ;

SHIMOMURA, K ;

MIZOTA, T ;

MATSUMOTO, S ;

MORI, J ;

KIKUCHI, H .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :607-611

[9] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .19 TAXONOMIC STUDIES ON THE PRODUCING STRAIN - A NEW SPECIES OF THE GENUS STREPTOMYCES [J].

IWAMI, M ;

KIYOTO, S ;

TERANO, H ;

KOHSAKA, M ;

AOKI, H ;

IMANAKA, H .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :589-593

[10] CLEAVAGE OF SULFONAMIDES WITH SODIUM NAPHTHALENE [J].

JI, S ;

GORTLER, LB ;

WARING, A ;

BATTISTI, A ;

BANK, S ;

CLOSSON, WD ;

WRIEDE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5311-&