Synthetic studies of 18-membered anti-tumor macrolide, tedanolide. Computer-aided conformational design of a seco-acid derivative for efficient macrolactonization

被引：52

作者：

Matsushima, T ^{[1
]}

Horita, K ^{[1
]}

Nakajima, N ^{[1
]}

Yonemitsu, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 03期

关键词：

D O I：

10.1016/0040-4039(95)02182-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Computer-aided conformational analyses are successfully applied to the synthesis of a key intermediary 18-membered lactone of tedanolide (I). The design of a seco-acid derivative based on computation in order to achieve its efficient macro-lactonization is described.

引用

页码：385 / 388

页数：4

共 12 条

[1] HOW MANY CONFORMERS ARE THERE FOR SMALL N-ALKANES - CONSEQUENCES OF ASYMMETRIC DEFORMATION IN GG SEGMENT [J].

GOTO, H ;

OSAWA, E ;

YAMATO, M .

TETRAHEDRON, 1993, 49 (02) :387-396

[2] AN EFFICIENT ALGORITHM FOR SEARCHING LOW-ENERGY CONFORMERS OF CYCLIC AND ACYCLIC MOLECULES [J].

GOTO, H ;

OSAWA, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (02) :187-198

[3]

GOTO H, 1992, TETRAHEDRON LETT, V33, P1343

[4] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .31. STEREOSELECTIVE SYNTHESIS OF ERYTHRONOLIDE A BY EXTREMELY EFFICIENT LACTONIZATION BASED ON CONFORMATIONAL ADJUSTMENT AND HIGH ACTIVATION OF SECO-ACID [J].

HIKOTA, M ;

TONE, H ;

HORITA, K ;

YONEMITSU, O .

TETRAHEDRON, 1990, 46 (13-14) :4613-4628

[5]

HIKOTA M, 1990, J ORG CHEM, V55, P9

[6] FLEXIBLE MOLECULES WITH DEFINED SHAPE - CONFORMATIONAL DESIGN [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) :1124-1134

[7]

HORITA K, IN PRESS TETRAHEDRON

[8] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[9]

NAKAJIMA N, 1991, CHEM PHARM BULL, V39, P64

[10] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .28. SYNTHESIS OF 16-MEMBERED MACROLIDE AGLYCONS, CARBONOLIDE-A, LEUCONOLIDES, AND MARIDONOLIDES, VIA CARBONOLIDE-B TYPE COMPOUNDS BY VIRTUE OF COMPLETELY STEREOSELECTIVE EPOXIDATION AND REDUCTION BASED ON THE CONFORMATIONAL CONTROL OF MACROLIDE RINGS WITH PROTECTING GROUPS [J].

NAKAJIMA, N ;

UOTO, K ;

MATSUSHIMA, T ;

YONEMITSU, O ;

GOTO, H ;

OSAWA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1129-1132

← 1 2 →