SYNTHESIS OF THE 9,10-ACETONIDE OF 9-DIHYDRO-FK-506

被引：41

作者：

IRELAND, RE

HIGHSMITH, TK

GEGNAS, LD

GLEASON, JL

机构：

[1] Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, McCormick Road

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the analog FKANAL (I) of the immunosuppressant FK-506 in Which the central features are the spiroenone system B which masks the alpha-allyl aldol portion of FK-506 and the spiroketal D which mimics the alpha-keto amide portion is described.

引用

收藏

页码：5071 / 5073

页数：3

相关论文

共 20 条

[1] PROBING IMMUNOSUPPRESSANT ACTION WITH A NONNATURAL IMMUNOPHILIN LIGAND [J].

BIERER, BE ;

SOMERS, PK ;

WANDLESS, TJ ;

BURAKOFF, SJ ;

SCHREIBER, SL .

SCIENCE, 1990, 250 (4980) :556-559

[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[3] ENANTIOSELECTIVE SYNTHESIS OF THE C(18)-C(35) SEGMENT OF IMMUNOSUPPRESSANT FK-506 USING EFFICIENT NEW METHODOLOGY [J].

COREY, EJ ;

HUANG, HC .

TETRAHEDRON LETTERS, 1989, 30 (39) :5235-5238

[4] A GENERAL-APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF SPIROKETALS - A TOTAL SYNTHESIS OF THE PHEROMONES OF THE OLIVE FRUIT-FLY AND RELATED-COMPOUNDS [J].

DESHONG, P ;

WALTERMIRE, RE ;

AMMON, HL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1901-1910

[5] REVERSED STEREOCHEMICAL CONTROL IN THE REGIOSELECTIVE REDUCTION OF HINDERED DIPHENYLPHOSPHINOYL (PH2PO-) KETONES AND ENONES [J].

ELLIOTT, J ;

HALL, D ;

WARREN, S .

TETRAHEDRON LETTERS, 1989, 30 (05) :601-604

[6]

FURSTNER A, 1989, J ORG CHEM, V54, P2307

[7]

HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4, P262

[8] METHODOLOGY FOR THE ENANTIOSELECTIVE SYNTHESIS OF ALDOLS AND OTHER 1,3-DIOXYGENATED SYSTEMS [J].

IRELAND, RE ;

WIPF, P ;

MILTZ, W ;

VANASSE, B .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1423-1424

[9] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF FK-506 - PREPARATION OF A C(1) TO C(15) SEGMENT [J].

IRELAND, RE ;

WIPF, P .

TETRAHEDRON LETTERS, 1989, 30 (08) :919-922

[10] CARBOALUMINATION OF 1-ALKYNES AND INSITU TRANSMETALATION TO HIGHER-ORDER CYANOCUPRATES - STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED AND DISUBSTITUTED OLEFINS BY CONJUGATE ADDITION TO ENONES [J].

IRELAND, RE ;

WIPF, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1425-1426