TOTAL SYNTHESIS OF 1233A

被引：73

作者：

WOVKULICH, PM

SHANKARAN, K

KIEGIEL, J

USKOKOVIC, MR

机构：

[1] Roche Research Center, Hoffmann-La Roche Inc., Nutley

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 04期

关键词：

D O I：

10.1021/jo00056a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.

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页码：832 / 839

页数：8

相关论文

共 63 条

[1]

ABELMAN MM, 1987, J ORG CHEM, V52, P4133

[2] ANTIBIOTIC-1233A - A FUNGAL BETA-LACTONE [J].

ALDRIDGE, DC ;

GILES, D ;

TURNER, WB .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (11) :639-&

[3] ANTIBIOTIC 1233A - FUNGAL BETA LACTONE [J].

ALDRIDGE, DC ;

GILES, D ;

TURNER, WB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23) :3888-&

[4] SYNTHESES OF TETRAHYDROLIPSTATIN AND ABSOLUTE-CONFIGURATION OF TETRAHYDROLIPSTATIN AND LIPSTATIN [J].

BARBIER, P ;

SCHNEIDER, F .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :196-202

[5] AN APPROACH TO THE SYNTHESIS OF THE HEXAHYDRONAPHTHALENE UNIT OF PRAVASTATIN [J].

BARRISH, JC ;

WOVKULICH, PM ;

TANG, PC ;

BATCHO, AD ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1990, 31 (16) :2235-2238

[6] SYNTHESIS OF TETRAHYDROLIPSTATIN [J].

CHADHA, NK ;

BATCHO, AD ;

TANG, PC ;

COURTNEY, LF ;

COOK, CM ;

WOVKULICH, PM ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4714-4718

[7]

CHALOVA OB, 1988, ZH PRIKL KHIM, V61, P934

[8] TOTAL SYNTHESIS OF L-659,699, A NOVEL INHIBITOR OF CHOLESTEROL-BIOSYNTHESIS [J].

CHIANG, YCP ;

YANG, SS ;

HECK, JV ;

CHABALA, JC ;

CHANG, MN .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5708-5712

[9] ABSOLUTE-CONFIGURATION OF L-659,699, A NOVEL INHIBITOR OF CHOLESTEROL-BIOSYNTHESIS [J].

CHIANG, YCP ;

CHANG, MN ;

YANG, SS ;

CHABALA, JC ;

HECK, JV .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4599-4603

[10] SIMPLE PROCEDURE FOR ELABORATION OF CARBONYL-COMPOUNDS INTO HOMOLOGOUS ALKYNES [J].

COLVIN, EW ;

HAMILL, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :869-874

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