REPLACEMENT OF THE NONPEROXIDIC TRIOXANE OXYGEN-ATOM OF ARTEMISININ BY CARBON - TOTAL SYNTHESIS OF (+)-13-CARBAARTEMISININ AND RELATED STRUCTURES

被引：23

作者：

AVERY, MA

FAN, PC

KARLE, JM

MILLER, R

GOINS, K

机构：

[1] UNIV MISSISSIPPI,SCH PHARM,PHARMACEUT SCI RES INST,UNIVERSITY,MS 38677

[2] UNIV N DAKOTA,DEPT CHEM,GRAND FORKS,ND 58202

[3] WALTER REED ARMY MED CTR,WALTER REED ARMY INST RES,DIV EXPTL THERAPEUT,WASHINGTON,DC 20307

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 23期

关键词：

D O I：

10.1016/0040-4039(95)00689-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Provided by total synthesis, endoperoxides 17, 19 and 21 underwent intramolecular oxymercuration-demercuration leading respectively to formation of an isomeric tetracycle, (1aS,3S,5aS,6R,8aS,9R,12S)-10-deoxo-13-carbaartemisinin 18, (+)-10-deoxo-13-carbaartemisinin 20, and (+)-13-carbaartemisinin 4. Neither target 4 nor 20 displayed substantial antimalarial potency in vitro against Plasmodium falciparum, but the isomeric peroxide 18 possessed reasonable antimalarial potency in vitro.

引用

页码：3965 / 3968

页数：4

共 9 条

[1]

Zaman, Sharma, Heterocycles, 32, pp. 1593-1638, (1991)

[2]

Jung, Current Med. Chem., 1, pp. 35-49, (1994)

[3]

Zhou, Xu, Accts. Chem. Res., 27, pp. 211-216, (1994)

[4]

Klayman, Science, 228, pp. 1049-1055, (1985)

[5]

Hong, Yang, Meshnick, Mol. Biochem. Parasitol., 63, pp. 121-128, (1994)

[6]

Posner, Oh, Wang, Gerena, Milhous, Meshnick, Asawamahasakdwa, J. Med. Chem., 37, pp. 1256-1258, (1994)

[7]

Posner, Oh, J. Amer. Chem. Soc., 114, pp. 8328-8329, (1992)

[8]

Asawamahasakdwa, Ittarat, Pu, Ziffer, Meshnick, Antimicrob. Agents Chemother., 38, pp. 1854-1858, (1994)

[9]

Jefford, 43rd Ann. Meeting of the Amer. Soc. Trop. Med. Hygiene, Second Generation Antimalarial Endoperoxides Symposium, (1994)

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