Stereoselective synthesis of the monomeric unit of SCH 351448

被引：15

作者：

Backes, J. Rene ^{[1
]}

Koert, Ulrich ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 12期

关键词：

stereoselective synthesis; natural product; SCH; 351448; tetrahydropyran;

D O I：

10.1002/ejoc.200600106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The monomeric unit of the macrodiolide SCH 351448 has been synthesized from three building blocks. Strategic disconnections were chosen between C21-C22 (Wittig) and C10-C11 (stereoselective aldol). The cis configuration of both 2,6-disubstituted tetrahydropyran rings was established by a stereoselective cationic reduction. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

引用

页码：2777 / 2785

页数：9

共 16 条

[1] Total synthesis of tartrolon B [J].

Berger, M ;

Mulzer, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (36) :8393-8394

[2] Efficient asymmetric synthesis of (+)-SCH 351448 [J].

Bolshakov, S ;

Leighton, JL .

ORGANIC LETTERS, 2005, 7 (17) :3809-3812

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5919-5923

[4] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[5] 1,5-asymmetric induction in methyl ketone aldol addition reactions [J].

Evans, DA ;

Coleman, PJ ;

Cote, B .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :788-789

[6]

GRIGORIEVA NY, 1989, SYNTHESIS-STUTTGART, P591

[7] A novel microbial metabolite, activator of low density lipoprotein receptor promoter [J].

Hegde, VR ;

Puar, MS ;

Dai, P ;

Patel, M ;

Gullo, VP ;

Das, PR ;

Bond, RW ;

McPhail, AT .

TETRAHEDRON LETTERS, 2000, 41 (09) :1351-1354

[8] NEW SYNTHESIS OF 2-ALKYLPYRROLIDINES AND 2-ALKYLPIPERIDINES [J].

HOUSE, HO ;

LEE, LF .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) :863-869

[9] CONFORMATIONAL PREFERENCE OF THE S=O GROUP .2. SYNTHESIS AND CONFORMATION OF 4,4,5,5-TETRAMETHYL-1,2-DITHIANE MONO-S-OXIDE [J].

JUARISTI, E ;

CRUZSANCHEZ, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3334-3338

[10] Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations [J].

Kang, EJ ;

Cho, EJ ;

Ji, MK ;

Lee, YE ;

Shin, DM ;

Choi, SY ;

Chung, YK ;

Kim, JS ;

Kim, HJ ;

Lee, SG ;

Lah, MS ;

Lee, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6321-6329

← 1 2 →