ChemInform Abstract: STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO ACETYLENIC ESTERS AND AMIDES, SYNTHESIS OF JUVENILE HORMONE ANALOGS

Anderson, R. J.; Corbin, Virginia L.; Cotterrell, G. P.; Cox, G. R.; Henrick, Clive A.; Schaub, F.; Siddall, J. B.

doi:10.1002/chin.197520133

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…25 Reaction of the latter with "MeCu" (prepared from methyllithium and CuI in THF and tetramethylethylenediamine) afforded geometrically pure (Z) a,~-unsaturated ester 17. 26 Reduction of this ester with diisobutylaluminum hydride in toluene-THF afforded the corresponding allylic alcohol, 18.…”

Section: The Chemical Stepsmentioning

confidence: 99%

α‐Multistriatin: The First Total Synthesis of a Natural Product via Antibody Catalysis

Sinha

Keinan

1996

Israel Journal of Chemistry

View full text Add to dashboard Cite

Abstract. The relevance of antibody catalysis to synthetic organic chemistry is demonstrated here by an efficient total synthesis of (-)-a-multistriatin, the aggregation pheromone of the European elm bark beetle, Scolytus multistriatus, which is the principal vector of the Dutch elm disease, responsible for the severe devastation of the elm population in Europe and North America. The key step in our synthesis of this natural product is an antibody-catalyzed, enantioselective protonolysis of an enol ether to produce a branched ketone. The latter is obtained with an (S) configuration in greater than 99% enantiomeric excess. Catalysis follows Michaelis-Menten kinetics (K m = 230 11M, k ca , = 0.36 min-I) and useful rate enhancement (kjk un = 65,000 at pH 6.5). This abzymic step is followed by twelve chemical steps, with all four asymmetric centers originating from the chirality achieved in the antibodycatalyzed reaction. That specific step is a unique example of a chemical transformation which is difficult to achieve either by an available synthetic methodology or via catalysis with a known enzyme. The synthetic pheromone has been checked in field experiments and found as active as the naturally occurring compound in attracting the European elm bark beetles.

show abstract

Section: The Chemical Stepsmentioning

confidence: 99%

α‐Multistriatin: The First Total Synthesis of a Natural Product via Antibody Catalysis

Sinha

Keinan

1996

Israel Journal of Chemistry

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO ACETYLENIC ESTERS AND AMIDES, SYNTHESIS OF JUVENILE HORMONE ANALOGS

Abstract: Die stereoselektive konjugierte Addition von verschiedenen Organo‐Cu(I)‐Reagenzien, wie z.B. (II), an Acetylencarbonsäureester, wie z.B. (I), zu Produkten wie (III) wird untersucht.

Cited by 1 publication

References 1 publication

α‐Multistriatin: The First Total Synthesis of a Natural Product via Antibody Catalysis

α‐Multistriatin: The First Total Synthesis of a Natural Product via Antibody Catalysis

Contact Info

Product

Resources

About