ASYMMETRIC TOTAL SYNTHESIS OF ISP-I (MYRIOCIN, THERMOZYMOCIDIN), A POTENT IMMUNOSUPPRESSIVE PRINCIPLE IN THE ISARIA-SINCLAIRII METABOLITE

被引：86

作者：

SANO, S

KOBAYASHI, Y

KONDO, T

TAKEBAYASHI, M

MARUYAMA, S

FUJITA, T

NAGAO, Y

机构：

[1] UNIV TOKUSHIMA,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN

[2] KYOTO PHARMACEUT UNIV,YAMASHIMA KU,KYOTO 607,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 12期

关键词：

D O I：

10.1016/0040-4039(95)00219-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric total synthesis of ISP-I has been achieved by utilizing highly selective E-olefin formation based on the Schlosser-modified Wittig reaction and highly diastereoselective aldol reactions employing both chiral heterocyclic derivatives, 3-acetyl-(4S)-isopropyl-1,3-thiazolidine-2-thione and ethyl [(5R)-2,5-dihydro-5-isopropyl-3,6-diethoxypyrazin]-2-yl carboxylate.

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页码：2097 / 2100

页数：4

相关论文

共 18 条

[1] ISOLATION AND STRUCTURE DETERMINATION OF A NEW ANTIFUNGAL ALPHA-HYDROXYMHTHYL-ALPHA-AMINO ACID [J].

ARAGOZZINI, F ;

CRAVERI, R ;

SCOLASTICO, C ;

RINDONE, B ;

MANACHINI, PL .

TETRAHEDRON, 1972, 28 (21) :5493-+

[2] 2-BENZOYLAMINO-2-DEOXY-2-HYDROXYMETHYL-D-HEXONO-1,4-LACTONES - SYNTHESIS FROM D-FRUCTOSE AND UTILIZATION IN THE TOTAL SYNTHESIS OF THERMOZYMOCIDIN (MYRIOCIN) [J].

BANFI, L ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1613-1619

[3]

CAREY FA, 1990, ADV ORG CHEM B, P95

[4] SYNTHESIS OF ALPHA-AZIDO ALDEHYDES - STEREOSELECTIVE FORMAL ACCESS TO THE IMMUNOSUPPRESSANT MYRIOCIN [J].

DELOISY, S ;

THANG, TT ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (27) :4783-4786

[5] CRYSTAL-STRUCTURE AND RELATIVE CONFIGURATION OF THE N-ACETYL-GAMMA-LACTONE OF THE ANTIFUNGAL ANTIBIOTIC THERMOZYMOCIDIN [J].

DESTRO, R ;

COLOMBO, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (07) :896-899

[6] FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE [J].

FUJITA, T ;

INOUE, K ;

YAMAMOTO, S ;

IKUMOTO, T ;

SASAKI, S ;

TOYAMA, R ;

CHIBA, K ;

HOSHINO, Y ;

OKUMOTO, T .

JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :208-215

[7] FUNGAL METABOLITES .12. POTENT IMMUNOSUPPRESSANT, 14-DEOXOMYRIOCIN, (2S,3R,4R)-(E)-2-AMINO-3,4-DIHYDROXY-2-HYDROXYMETHYLEICOS-6-ENOIC ACID AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF MYRIOCIN DERIVATIVES [J].

FUJITA, T ;

INOUE, K ;

YAMAMOTO, S ;

IKUMOTO, T ;

SASAKI, S ;

TOYAMA, R ;

YONETA, M ;

CHIBA, K ;

HOSHINO, Y ;

OKUMOTO, T .

JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :216-224

[8] THE SYNTHESIS OF THE (-)-ENANTIOMER OF (+)-ANHYDROMYRIOCIN FIGURE-15, THE GAMMA-LACTONE DERIVED FROM MYRIOCIN (THERMOZYMOCIDIN) [J].

JUST, G ;

PAYETTE, DR .

TETRAHEDRON LETTERS, 1980, 21 (34) :3219-3222

[9] MYRIOCIN, A NEW ANTIFUNGAL ANTIBIOTIC FROM MYRIOCOCCUM-ALBOMYCES [J].

KLUEPFEL, D ;

VEZINA, C ;

SEHGAL, SN ;

KUDELSKI, A ;

CHAREST, MP ;

BAGLI, J .

JOURNAL OF ANTIBIOTICS, 1972, 25 (02) :109-+

[10] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482