ISONITRILES FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE

被引：33

作者：

CARMELI, S

MOORE, RE

PATTERSON, GML

MORI, Y

SUZUKI, M

机构：

[1] UNIV HAWAII,DEPT CHEM,HONOLULU,HI 96822

[2] MEIJO UNIV,FAC PHARM,TEMPAKU KU,NAGOYA,AICHI 468,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 14期

关键词：

D O I：

10.1021/jo00301a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An aerial form of Scytonema mirabile (Dillwyn) Bornet, designated strain number BY-8-1, has been found to contain six novel isonitriles, viz. mirabilene isonitriles A-F (7—12), which are mildly cytotoxic and antimicrobial. The gross structures of 7–12 were determined by detailed spectral analysis. The relative and absolute stereochemistry of 7–12 were solved by chemical degradation and direct comparison of degradation products with synthetic samples; mirabilene-A isonitrile (7), for example, was degraded to methyl (3R,5/?,7S,9S)-3,5,7,9-tetrameth-oxy-10-oxoundecanal (15) and isopropyl (S)-3-trifluoroacetamidobutyrate (14), which indicated that the absolute configurations of C-4, C-6, C-8, C-10, and C-16 in 7 were all S. © 1990, American Chemical Society. All rights reserved.

引用

页码：4431 / 4438

页数：8

共 12 条

[1] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].