Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy

被引：28

作者：

Li, Fangzheng ^{[1
]}

Miller, Marvin J. ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 14期

关键词：

D O I：

10.1021/jo060555y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

引用

页码：5221 / 5227

页数：7

共 26 条

[1] Synthesis of C-19-functionalized 1α-hydroxyvitamin D2 analogues via ring-closing metathesis [J].

Ahmed, M ;

Atkinson, CE ;

Barrett, AGM ;

Malagu, K ;

Procopiou, PA .

ORGANIC LETTERS, 2003, 5 (05) :669-672

[2] Synthesis of an oxaspirolactone intermediate for the synthesis of spirolides [J].

Brimble, MA ;

Fares, FA ;

Turner, P .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (10) :845-851

[3] A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis [J].

Chang, SB ;

Grubbs, RH .

TETRAHEDRON LETTERS, 1997, 38 (27) :4757-4760

[4]

CHEN W, 2003, 226 ACS NAT M SEP 7

[5] METABOLISM PRODUCTS OF MICROORGANISMS .205. ISOLATION AND STRUCTURE OF STREPTAZOLIN [J].

DRAUTZ, H ;

ZAHNER, H ;

KUPFER, E ;

KELLERSCHIERLEIN, W .

HELVETICA CHIMICA ACTA, 1981, 64 (06) :1752-1765

[6] ENANTIOSELECTIVE TOTAL SYNTHESIS OF STREPTAZOLIN - THE TANDEM USE OF IMINIUM ION VINYLSILANE CYCLIZATIONS AND INTRAMOLECULAR ACYLATIONS [J].

FLANN, CJ ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6115-6118

[7] SECONDARY METABOLITES BY CHEMICAL-SCREENING .21. CLONOSTACHYDIOL, A NOVEL ANTHELMINTIC MACRODIOLIDE FROM THE FUNGUS CLONOSTACHYS-CYLINDROSPORA (STRAIN FH-A-6607) [J].

GRABLEY, S ;

HAMMANN, P ;

THIERICKE, R ;

WINK, J ;

PHILIPPS, S ;

ZEECK, A .

JOURNAL OF ANTIBIOTICS, 1993, 46 (02) :343-345

[8] SECONDARY METABOLITES BY CHEMICAL-SCREENING .4. DETECTION, ISOLATION AND BIOLOGICAL-ACTIVITIES OF CHIRAL SYNTHONS FROM STREPTOMYCES [J].

GRABLEY, S ;

HAMMANN, P ;

KLUGE, H ;

WINK, J ;

KRICKE, P ;

ZEECK, A .

JOURNAL OF ANTIBIOTICS, 1991, 44 (07) :797-800

[9] NEW LEAD STRUCTURES BY DIELS-ALDER REACTIONS OF STREPTAZOLIN WITH NAPHTHOQUINONES [J].

GRABLEY, S ;

KLUGE, H ;

HOPPE, HU .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (07) :664-665

[10] Total synthesis of (+)-streptazolin [J].

Huang, SL ;

Comins, DL .

CHEMICAL COMMUNICATIONS, 2000, (07) :569-570

← 1 2 3 →