ABSOLUTE STRUCTURE AND TOTAL SYNTHESIS OF LIPOGRAMMISTIN-A, A LIPOPHILIC ICHTHYOTOXIN OF THE SOAPFISH

Authors
ONUKI H ITO K KOBAYASHI Y MATSUMORI N TACHIBANA K FUSETANI N
Citation
H. Onuki et al., ABSOLUTE STRUCTURE AND TOTAL SYNTHESIS OF LIPOGRAMMISTIN-A, A LIPOPHILIC ICHTHYOTOXIN OF THE SOAPFISH, Journal of organic chemistry, 63(12), 1998, pp. 3925-3932
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
12
Year of publication
1998
Pages
3925 - 3932
Database
ISI
SICI code
0022-3263(1998)63:12<3925:ASATSO>2.0.ZU;2-L
Abstract
Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic co nstituent of the skin mucus of the grammistid fish Aulacocephalus temm incki. Its absolute stereochemistry was established by chemical degrad ation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysi s of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two di astereomers (4S)- and (4R)-1.