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

被引：14

作者：

NAKAJIMA, N

UOTO, K

MATSUSHIMA, T

YONEMITSU, O

GOTO, H

OSAWA, E

机构：

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

[2] HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 04期

关键词：

D O I：

10.1021/jo00291a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbonolide B type compounds were converted to seven typical 16-membered macrolide aglycons, carbonolide A, EOP aglycon, leuconolide A1 and A3, midecanolide A1, and maridonolide II and I, by virtue of completely stereoselective epoxidation and/or reduction based on the conformational control of macrolide rings with protecting groups. NOE and NOESY measurements and MMP2-CONFLEX2 calculations were employed to predict the conformation of the carbonolide B type compounds. © 1990, American Chemical Society. All rights reserved.

引用

页码：1129 / 1132

页数：4

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