TY - JOUR
T1 - Isonitriles from the Blue-Green Alga Scytonema mirabile
AU - Carmeli, Shmuel
AU - Moore, Richard E.
AU - Patterson, Gregory M.L.
AU - Mori, Yuji
AU - Suzuki, Makoto
PY - 1990
Y1 - 1990
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0001600261&partnerID=8YFLogxK
U2 - 10.1021/jo00301a041
DO - 10.1021/jo00301a041
M3 - מאמר
AN - SCOPUS:0001600261
VL - 55
SP - 4431
EP - 4438
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -