Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: Organometallic coupling versus standard macrolactonization

被引：28

作者：

Coleman, RS ^{[1
]}

Garg, R ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 22期

关键词：

D O I：

10.1021/ol016744e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Stereocontrolled construction of the 12-membered diene and triene lactones 1, 2, and 3, characteristic of the antitumor agent oximidines I and II, are reported and were based on an intramolecular Castro-Stephens coupling for the construction of a cyclic enyne or dienyne followed by stereoselective reduction of the cyclic alkyne for introduction of the cis-olefin of the targets. A comparison of the effectiveness of this protocol is made with standard macrolactonization.

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页码：3487 / 3490

页数：4

相关论文

共 23 条

[1] REGIO-SPECIFIC AND STEREO-SPECIFIC REDUCTION OF CONJUGATED AND NON-CONJUGATED TRIPLE BONDS BY ACTIVATED ZINC POWDER [J].

AERSSENS, MHPJ ;

BRANDSMA, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (12) :735-736

[2]

BARRY J, 1985, SYNTHESIS-STUTTGART, P40

[3]

Boyd MR, 2001, J PHARMACOL EXP THER, V297, P114

[4] HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS [J].

BRANDES, BD ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4378-4380

[5] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].

Erickson, KL ;

Beutler, JA ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192

[6] VINYL CATIONS .42. SYNTHESIS AND SOLVOLYSIS OF SUBSTITUTED 1-CYCLOBUTENYL NONAFLATES [J].

HANACK, M ;

AUCHTER, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5238-5245

[7] TOTAL SYNTHESIS OF CALICHEAMICINONE - NEW ARRANGEMENTS FOR ACTUATION OF THE REDUCTIVE CYCLOAROMATIZATION OF AGLYCON CONGENERS [J].

HASELTINE, JN ;

CABAL, MP ;

MANTLO, NB ;

IWASAWA, N ;

YAMASHITA, DS ;

COLEMAN, RS ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3850-3866

[8] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[9] ASYMMETRIC DIHYDROXYLATION OF ENYNES [J].

JEONG, KS ;

SJO, P ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1992, 33 (27) :3833-3836

[10] Oximidines I and II:: Novel antitumor macrolides from Pseudomonas sp. [J].

Kim, JW ;

Shin-ya, K ;

Furihata, K ;

Hayakawa, Y ;

Seto, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :153-155