TOTAL SYNTHESIS OF (+/-)-PHASEIC ACID

被引：19

作者：

ABRAMS, GD

ABRAMS, SR

NELSON, LAK

GUSTA, LV

机构：

[1] NATL RES COUNCIL CANADA,INST PLANT BIOTECHNOL,110 GYMNASIUM PL,SASKATOON S7N 0W9,SASKATCHEWAN,CANADA

[2] UNIV SASKATCHEWAN,CTR CROP DEV,SASKATOON S7N 0W0,SASKATCHEWAN,CANADA

来源：

TETRAHEDRON | 1990年 / 46卷 / 16期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4020(01)87752-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of (±)-phaseic acid is described. Photochemical reaction of the nitrite derived from trans-4-hydroxy-2,2,6-trimethylcyclohexanone functionalizes the methyl group of the geminal pair cis to the hydroxyl group of the starting alcohol. The oxime formed is converted in four steps to a conjugated 6-oxabicyclo[3.2.1]octenone, to which the side chain synthon is added as an alkynyl lithium to give a single adduct in high yield. Further transformation yields (±)-phaseic acid free of its unwanted epimer. © 1990.

引用

收藏

页码：5543 / 5554

页数：12

相关论文

共 16 条

[1] A NEW PHOTOCHEMICAL REACTION [J].

BARTON, DH ;

BEATON, JM ;

GELLER, LE ;

PECHET, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (19) :4076-&

[2] NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS [J].

COREY, EJ ;

GILMAN, NW ;

GANEM, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5616-&

[3] TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN [J].

COREY, EJ ;

SNIDER, BB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) :2549-&

[4]

DERGUINI F, 1974, TETRAHEDRON LETT, P4899

[5] HYDROLYSIS, NITROSYL EXCHANGE, AND SYNTHESIS OF ALKYL NITRITES [J].

DOYLE, MP ;

TERPSTRA, JW ;

PICKERING, RA ;

LEPOIRE, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3379-3382

[6] SYNTHESEN IN DER CAROTINOID-REIHE .7. TOTALSYNTHESE VON ZEAXANTHIN UND PHYSALIEN [J].

ISLER, O ;

LINDLAR, H ;

MONTAVON, M ;

RUEGG, R ;

SAUCY, G ;

ZELLER, P .

HELVETICA CHIMICA ACTA, 1956, 39 (07) :2041-2053

[7] SYNTHESIS OF MONOTERPENOIDS AND SESQUITERPENOIDS .17. STEREOCONTROLLED SYNTHESIS OF BOTH THE NANTIOMERS OF PHASEIC ACID AND ITS METHYL-ESTER, A PIVOTAL METABOLITE OF ABSCISIC-ACID [J].

KITAHARA, T ;

TOUHARA, K ;

WATANABE, H ;

MORI, K .

TETRAHEDRON, 1989, 45 (20) :6387-6400

[8] SYNTHESIS OF OPTICALLY-ACTIVE NATURAL CAROTENOIDS AND STRUCTURALLY RELATED COMPOUNDS .1. SYNTHESIS OF CHIRAL KEY COMPOUND (4R,6R)-4-HYDROXY-2,2,6-TRIMETHYLCYCLOHEXANONE [J].

LEUENBERGER, HGW ;

BOGUTH, W ;

WIDMER, E ;

ZELL, R .

HELVETICA CHIMICA ACTA, 1976, 59 (05) :1832-1849

[9]

LOVEYS BR, 1984, SOC EXP BIOL SEMIN S, V23, P71

[10]

MACMILLAN J, 1968, J CHEM SOC CHEM COMM, P124