Synthesis of a 6-azaspiro[4.5]decane related to halichlorine and the pinnaic acids

被引：52

作者：

Clive, DLJ ^{[1
]}

Yeh, VSC ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(99)01815-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfone 15, derived from D-glutamic acid, and aldehyde 23, made by diastereoselective alkylation, were linked and elaborated into enamine sulfone 33. This underwent 5-exo radical cyclization to 34, which was desulfonylated to (-)-35, a compound that represents the spirobicyclic core of halichlorine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8503 / 8507

页数：5

相关论文

共 22 条

[1] Absolute stereochemistry of halichlorine; A potent inhibitor of VCAM-1 induction [J].

Arimoto, H ;

Hayakawa, I ;

Kuramoto, M ;

Uemura, D .

TETRAHEDRON LETTERS, 1998, 39 (08) :861-862

[2] Synthesis of pinnaic acid; Asymmetric construction of spirocyclic core [J].

Arimoto, H ;

Asano, S ;

Uemura, D .

TETRAHEDRON LETTERS, 1999, 40 (18) :3583-3586

[3]

BARTLETT PA, 1970, TETRAHEDRON LETT, P4459

[4] Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata [J].

Chou, T ;

Kuramoto, M ;

Otani, Y ;

Shikano, M ;

Yazawa, K ;

Uemura, D .

TETRAHEDRON LETTERS, 1996, 37 (22) :3871-3874

[5] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].

EVANS, DA ;

URPI, F ;

SOMERS, TC ;

CLARK, JS ;

BILODEAU, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216

[6] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].

EVANS, DA ;

KALDOR, SW ;

JONES, TK ;

CLARDY, J ;

STOUT, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031

[7]

GAGE JR, 1989, ORG SYNTH, V68, P77

[8] Synthetic studies on the azinothricin family of antitumour antibiotics .5. Asymmetric synthesis of two activated esters for the northern sector of A83586C [J].

Hale, KJ ;

Cai, JQ .

TETRAHEDRON LETTERS, 1996, 37 (24) :4233-4236

[9] Stereocontrolled total synthesis of an annonacin A-type acetogenin: Pseudoannonacin A? [J].

Hanessian, S ;

Grillo, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1049-1057

[10] SYNTHESEN IN DER CAROTINOID-REIHE .10. MITTEILUNG - ANWENDUNG DER WITTIG-REAKTION ZUR SYNTHESE VON ESTERN DES BIXINS UND CROCETINS [J].

ISLER, O ;

GUTMANN, H ;

MONTAVON, M ;

RUEGG, R ;

RYSER, G ;

ZELLER, P .

HELVETICA CHIMICA ACTA, 1957, 40 (05) :1242-&