Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755).
A stereoselective total synthesis of the natural antibiotic (-)-8-O-methyltetrangomycin 1 is reported. The essential steps for this convergent synthesis are the transformation of a geraniol epoxide into a chiral octadiyne derivative, which was converted into a triyne. The cobalt-mediated [2+2+2] cycloaddition of the triyne led to a benz[a]anthracene system, which was oxidized with Ag(Py)(2)MnO(4) to a benz[a]anthraquinone. Deprotection with aqueous HF in acetonitrile and photooxidation afforded the desired product (-)-1. [reaction: see text]
Kesenheimer
Christian
C
Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstrasse 10, 78457 Konstanz, Germany.
Groth
Ulrich
U
D000080462:Acyclic Monoterpenes; D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry; D000095602:Angucyclines and Angucyclinones
D000080462:Acyclic Monoterpenes; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D013729:Terpenes; C059960:MM 47755; D000095602:Angucyclines and Angucyclinones; C007836:geraniol