Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

被引：24

作者：

Garcia, J ^{[1
]}

López, M ^{[1
]}

Romeu, J ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Div 3, E-08028 Barcelona, Catalonia, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(99)00251-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2617 / 2626

页数：10

共 36 条

[1] FURTHER BIOACTIVE ACETYLENIC-COMPOUNDS FROM THE CARIBBEAN SPONGE CRIBROCHALINA-VASCULUM [J].

AIELLO, A ;

FATTORUSSO, E ;

MENNA, M .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (09) :1275-1280

[2] Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: Useful intermediates for the synthesis of optically active gamma-lactones [J].

Allevi, P ;

Ciuffreda, P ;

Anastasia, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :93-99

[3] Oxazaborolidine-catalysed reduction of alk-2-ene-1,4diones.: A convenient access to chiral 1,4-diols [J].

Bach, J ;

Berenguer, R ;

Garcia, J ;

López, M ;

Manzanal, J ;

Vilarrasa, J .

TETRAHEDRON, 1998, 54 (49) :14947-14962

[4] ALLYLIC ALCOHOLS OF UNEXPECTED CONFIGURATION BY OXAZABOROLIDINE-CATALYZED REDUCTION OF ALPHA,BETA-UNSATURATED KETONES - AN EXPLANATION-BASED ON MO CALCULATIONS [J].

BACH, J ;

BERENGUER, R ;

FARRAS, J ;

GARCIA, J ;

MESEGUER, J ;

VILARRASA, J .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2683-2686

[5] A SYNTHETIC APPROACH TOWARDS OCTALACTIN-A, BASED ON THE STEREOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES [J].

BACH, J ;

BERENGUER, R ;

GARCIA, J ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1995, 36 (19) :3425-3428

[6] Highly enantioenriched propargylic alcohols by oxazaborolidine-mediated reduction of acetylenic ketones [J].

Bach, J ;

Berenguer, R ;

Garcia, J ;

Loscertales, T ;

Vilarrasa, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9021-9025

[7] Stereoselective reduction of α′-branched α,β-ynones.: Application to the synthesis of the Octalactin A ring [J].

Bach, J ;

Garcia, J .

TETRAHEDRON LETTERS, 1998, 39 (37) :6761-6764

[8] SELECTIVE REDUCTIONS .37. ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH B-(3-PINANYL)-9-BORABICYCLO[3.3.1]NONANE [J].

BROWN, HC ;

PAI, GG .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1384-1394

[9] FURTHER HIGH MOLECULAR-WEIGHT POLYACETYLENES FROM THE SPONGE PETROSIA-FICIFORMIS [J].

CIMINO, G ;

DEGIULIO, A ;

DEROSA, S ;

DESTEFANO, S ;

SODANO, G .

JOURNAL OF NATURAL PRODUCTS, 1985, 48 (01) :22-27

[10]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

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