A concise semi-synthetic approach to betulinic acid from betulin

被引：153

作者：

Kim, DSHL

Chen, ZD

Nguyen, VT

Pezzuto, JM

Qiu, SX

Lu, ZZ

机构：

[1] Dept. of Med. Chem. and Pharmacog., College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612-7231

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 09期

关键词：

D O I：

10.1080/00397919708006099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Betulin was convert to betulinic acid using two different synthetic routes. The first approach involved an oxidation of betulin using Jones' reagent to betulonic acid and subsequent NaBH4 reduction to betulinic acid. The second approach involved steps utilizing different protecting groups on the alcohol functional groups of betulin and Jones' oxidation to circumvent the isomerization of the secondary alcohol of betulinic acid.

引用

页码：1607 / 1612

页数：6

共 8 条

[1] CHEMISTRY OF TRITERPENES AND RELATED COMPOUNDS .43. CONSTITUENTS OF BARK OF PLATANUS X HYBRIDA BROT AND STRUCTURE OF PLATANIC ACID [J].

APLIN, RT ;

HALSALL, TG ;

NORIN, T .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, :3269-&

[2] ANTI-AIDS AGENTS .11. BETULINIC ACID AND PLATANIC ACID AS ANTI-HIV PRINCIPLES FROM SYZIGIUM-CLAVIFLORUM, AND THE ANTI-HIV ACTIVITY OF STRUCTURALLY RELATED TRITERPENOIDS [J].

FUJIOKA, T ;

KASHIWADA, Y ;

KILKUSKIE, RE ;

COSENTINO, LM ;

BALLAS, LM ;

JIANG, JB ;

JANZEN, WP ;

CHEN, IS ;

LEE, KH .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :243-247

[3] SOME CONSTITUENTS OF AKANIA LUCENS [J].

KRAJNIAK, E ;

RITCHIE, E ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (06) :1331-&

[4] STUDIES ON INDIAN MEDICINAL PLANTS .18. NON-ALKALOIDAL CONSTITUENTS FROM SEEDS OF ALANGIUM LAMARCKII THW [J].

PAKRASHI, SC ;

BHATTACHARYYA, J ;

MOOKERJEE, S ;

SAMANTA, TB ;

VORBRUGGEN, H .

PHYTOCHEMISTRY, 1968, 7 (03) :461-+

[5] DISCOVERY OF BETULINIC ACID AS A SELECTIVE INHIBITOR OF HUMAN-MELANOMA THAT FUNCTIONS BY INDUCTION OF APOPTOSIS [J].

PISHA, E ;

CHAI, H ;

LEE, IS ;

CHAGWEDERA, TE ;

FARNSWORTH, NR ;

CORDELL, GA ;

BEECHER, CWW ;

FONG, HHS ;

KINGHORN, AD ;

BROWN, DM ;

WANI, MC ;

WALL, ME ;

HIEKEN, TJ ;

DASGUPTA, TK ;

PEZZUTO, JM .

NATURE MEDICINE, 1995, 1 (10) :1046-1051

[6] SYNTHESIS OF SOME DE AND CDE RING ANALOGS OF CAMPTOTHECIN [J].

PLATTNER, JJ ;

GLESS, RD ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (24) :8613-&

[7] Polyterpenoid compounds - Part I Betulic acid from Cornus floridal, L [J].

Robertson, A ;

Soliman, G ;

Owen, EC .

JOURNAL OF THE CHEMICAL SOCIETY, 1939, :1267-1273

[8]

VONRUZICKA L, 1938, HELV CHIM ACTA, V21, P1706

← 1 →