Synthetic studies on virantmycin .2. Total synthesis of unnatural (+)-virantmycin and determination of its absolute stereochemistry

被引：37

作者：

Morimoto, Y ^{[1
]}

Shirahama, H ^{[1
]}

机构：

[1] KWANSEI GAKUIN UNIV,SCH SCI,DEPT CHEM,NISHINOMIYA,HYOGO 662,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 32期

关键词：

D O I：

10.1016/0040-4020(96)00608-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective total synthesis of (+)-virantmycin (1) has been achieved by means of the Sharpless asymmetric epoxidation of allylic alcohol 27 followed by an intramolecular epoxide opening of the exo epoxy alcohol 32 which was derived from the endo epoxy alcohol 28. The synthesis of (+)-1 has established that the absolute configuration of the natural product (-)-1 is shown to be 2R, 3R at the two chiral centers. Further, antiviral activities of the virantmycin analogs were also examined against influenza virus. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：10631 / 10652

页数：22

共 35 条

[21] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[22] ASSIGNMENT OF ABSOLUTE-CONFIGURATION FOR VIRANTMYCIN AND SYNTHESIS OF ITS ANTIPODE [J].

MORIMOTO, Y ;

ODA, K ;

SHIRAHAMA, H ;

MATSUMOTO, T ;

OMURA, S .

CHEMISTRY LETTERS, 1988, (06) :909-912

[23] CONVENIENT METHOD FOR SYNTHESIS OF CARBOXYLIC ESTERS [J].

MUKAIYAMA, T ;

USUI, M ;

SHIMADA, E ;

SAIGO, K .

CHEMISTRY LETTERS, 1975, (10) :1045-1048

[24] VIRANTMYCIN - A NEW ANTIVIRAL ANTIBIOTIC PRODUCED BY A STRAIN OF STREPTOMYCES [J].

NAKAGAWA, A ;

IWAI, Y ;

HASHIMOTO, H ;

MIYAZAKI, N ;

OIWA, R ;

TAKAHASHI, Y ;

HIRANO, A ;

SHIBUKAWA, N ;

KOJIMA, Y ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1981, 34 (11) :1408-1415

[25] ACTIVATION OF 7-ENDO OVER 6-EXO EPOXIDE OPENINGS - SYNTHESIS OF OXEPANE AND TETRAHYDROPYRAN SYSTEMS [J].

NICOLAOU, KC ;

PRASAD, CVC ;

SOMERS, PK ;

HWANG, CK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5335-5340

[26] ACTIVATION OF 6-ENDO OVER 5-EXO HYDROXY EPOXIDE OPENINGS - STEREOSELECTIVE AND RING SELECTIVE SYNTHESIS OF TETRAHYDROFURAN AND TETRAHYDROPYRAN SYSTEMS [J].

NICOLAOU, KC ;

PRASAD, CVC ;

SOMERS, PK ;

HWANG, CK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5330-5334

[27] STRUCTURE OF VIRANTMYCIN, A NOVEL ANTI-VIRAL ANTIBIOTIC [J].

OMURA, S ;

NAKAGAWA, A .

TETRAHEDRON LETTERS, 1981, 22 (23) :2199-2202

[28] VIRANTMYCIN, A POTENT ANTI-VIRAL ANTIBIOTIC PRODUCED BY A STRAIN OF STREPTOMYCES [J].

OMURA, S ;

NAKAGAWA, A ;

HASHIMOTO, H ;

OIWA, R ;

IWAI, Y ;

HIRANO, A ;

SHIBUKAWA, N ;

KOJIMA, Y .

JOURNAL OF ANTIBIOTICS, 1980, 33 (11) :1395-1396

[29] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].

PAPPO, R ;

ALLEN, DS ;

LEMIEUX, RU ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479

[30] STEREOCHEMISTRY OF (-)-VIRANTMYCIN [J].

PEARCE, CM ;

SANDERS, JKM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :409-411

← 1 2 3 4 →