TOTAL SYNTHESIS OF (+/-)-9-DEOXYGONIOPYPYRONE

被引：16

作者：

FRIESEN, RW

BISSADA, S

机构：

[1] Department of Medicinal Chemistry, Pointe Claire-Dorval, Que. H9R 4P8

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)77261-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-9-deoxygoniopypyrone (1) from the alpha-allenic alcohol 2 is described. The synthesis is accomplished in 10 steps with the relative configuration of the three contiguous asymmetric centers being established by the highly diastereoselective formation of the synvicinal diet 3 via the iodo-cyclofunctionalization reaction of the allenic carbamate 5 and the epoxidation of the olefinic acetonide 11.

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页码：5615 / 5618

页数：4

相关论文

共 11 条

[1] NOVEL BIOACTIVE STYRYL-LACTONES - GONIOFUFURONE, GONIOPYPYRONE, AND 8-ACETYLGONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) - X-RAY MOLECULAR-STRUCTURE OF GONIOFUFURONE AND OF GONIOPYPYRONE [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

FANWICK, PE ;

MCLAUGHLIN, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1655-1661

[2] 2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

MCLAUGHLIN, JL ;

FANWICK, PE .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1034-1043

[3] IODOCYCLIZATION OF THE (TOLYLSULFONYL)CARBAMATES AND (TRICHLOROACETYL)CARBAMATES OF SECONDARY ALPHA-ALLENIC ALCOHOLS - HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF SYN-1,2-AMINO ALCOHOLS AND TRANS-5-ALKYL-2-OXO-OXAZOLIDINE-4-CARBOXYLIC ACIDS [J].

FRIESEN, RW ;

KOLACZEWSKA, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4888-4895

[4] A HIGHLY STEREOSELECTIVE PREPARATION OF A NOVEL CLASS OF VINYL EPOXIDES FROM ALPHA-ALLENIC ALCOHOLS [J].

FRIESEN, RW ;

BLOUIN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1653-1654

[5] A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA-ALLENIC ALCOHOLS TO SYN-1,2-DIOL DERIVATIVES [J].

FRIESEN, RW ;

GIROUX, A .

TETRAHEDRON LETTERS, 1993, 34 (12) :1867-1870

[6] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].

HOVEYDA, AH ;

EVANS, DA ;

FU, GC .

CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370

[7]

Johnson R.A., 1993, CATALYTIC ASYMMETRIC

[8] EFFICACIOUS MODIFICATION OF THE MITSUNOBU REACTION FOR INVERSIONS OF STERICALLY HINDERED SECONDARY ALCOHOLS [J].

MARTIN, SF ;

DODGE, JA .

TETRAHEDRON LETTERS, 1991, 32 (26) :3017-3020

[9] STUDIES ON THE TOTAL SYNTHESIS OF SESBANIMIDE - A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THE AB RING-SYSTEM [J].

ROUSH, WR ;

MICHAELIDES, MR .

TETRAHEDRON LETTERS, 1986, 27 (29) :3353-3356

[10]

Sharpless K. B., 1979, ALDRICHIM ACTA, V12, P63