CALYCULINS - ASYMMETRIC-SYNTHESIS OF THE C-26-C-32 FRAGMENT

被引：24

作者：

KOSKINEN, AMP

PIHKO, PM

机构：

[1] Department of Chemistry, University of Oulu, FIN-90570 Oulu, Linnanmaa

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 40期

关键词：

D O I：

10.1016/0040-4039(94)85330-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and highly stereocontrolled method for the construction of the natural syn stereochemistry at C-30 and C-32 in the calyculin C oxazole fragment has been devised starting from alanine. The title fragment itself is accessible in seven steps from N-BOC-alaninal.

引用

收藏

页码：7417 / 7420

页数：4

相关论文

共 29 条

[1] STEREOSELECTIVE METHYLATIONS OF BICYCLIC LACTAMS DERIVED FROM PYROGLUTAMIC ACID [J].

ARMSTRONG, RW ;

DEMATTEI, JA .

TETRAHEDRON LETTERS, 1991, 32 (41) :5749-5752

[2] STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(15)-C(25) SPIROKETAL UNIT [J].

BARRETT, AGM ;

EDMUNDS, JJ ;

HORITA, K ;

PARKINSON, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1236-1238

[3] STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(26)-C(37) AMIDE OXAZOLE UNIT [J].

BARRETT, AGM ;

EDMUNDS, JJ ;

HENDRIX, JA ;

MALECHA, JW ;

PARKINSON, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1240-1242

[4] STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(1)-C(14) TETRAENE NITRILE UNIT [J].

BARRETT, AGM ;

EDMUNDS, JJ ;

HENDRIX, JA ;

HORITA, K ;

PARKINSON, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1238-1240

[5] CUPRIC BROMIDE MEDIATED OXIDATION OF 4-CARBOXYOXAZOLINES TO THE CORRESPONDING OXAZOLES [J].

BARRISH, JC ;

SINGH, J ;

SPERGEL, SH ;

HAN, WC ;

KISSICK, TP ;

KRONENTHAL, DR ;

MUELLER, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4494-4496

[6] OKADAIC ACID - A NEW PROBE FOR THE STUDY OF CELLULAR-REGULATION [J].

COHEN, P ;

HOLMES, CFB ;

TSUKITANI, Y .

TRENDS IN BIOCHEMICAL SCIENCES, 1990, 15 (03) :98-102

[7] TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453

[8] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .96. STEREOSELECTIVE SYNTHESIS OF 2,3-DIHYDROXY-4-DIMETHYLAMINO-5-METHOXYPENTANOIC ACID, A FRAGMENT OF CALYCULINS - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CALYCULINS [J].

HAMADA, Y ;

TANADA, Y ;

YOKOKAWA, F ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1991, 32 (42) :5983-5986

[9]

HAMADA Y, 1982, CHEM PHARM BULL, V30, P1921

[10]

HARA O, 1991, SYNLETT, P285