112709-47-4

Upstream product

• 111917-97-6 (+/-)-Periplanon D₁ 
• 593-71-5 Chloroiodomethane 
• 70552-79-3 (2Z,6E,8S)-10-t-butyldimethylsilyloxy-8-isopropyl-5-methylene-2,6-cyclodecadien-1-one 
• 2181-42-2 trimethylsulphonium iodide 
• 113666-35-6 (2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one 
• 120913-03-3 C₂₄H₃₂N₂O₄S 
• 120913-02-2 Acetic acid (E)-(1R,3R)-3-isopropyl-6,10-dimethylene-9-oxo-cyclodec-4-enyl ester 
• 116363-89-4 (3Z,7E)-(1S,9S)-9-Isopropyl-2,6-dimethylene-cyclodeca-3,7-dienol 
• 105990-54-3 C₂₀H₃₄O₂Si 
• 111917-96-5 tert-Butyl-((3Z,7E)-9-isopropyl-2,6-dimethylene-cyclodeca-3,7-dienyloxy)-dimethyl-silane 
• 113581-00-3 germacrone 

Downstream Products

• 69239-67-4 Persoon's periplanone-A 

Relevant academic research and scientific papers

X-Ray Crystallographic and NOE Studies on the Conformation of Periplanones and their Analogues

The structure of periplanone-A was established by X-ray crystallographic analysis.In comparison of the X-ray and 1H NMR data with those of periplanone-B, it was shown that periplanone-A and -B adopt essentially the same conformation.The epoxy epimer of periplanone-A has 104-times lower biological activity than periplanone-A, and NMR analysis indicated that the molecule exists in a mixture of different conformers.The conformation of the regioisomer, in which the carbonyl and epoxy groups are transposed, was analysed by X-ray crystallography and 1H NMR spectroscopy.It is highly biologically active, and the conformation of the germacranoid skeleton was shown to be almost identical with that of periplanone-A.Simplified analogues and germacrene-D had relatively lower activity.NOE Experiments on these compounds suggested the conformational resemblance of their germacranoid skeletons with those of periplanone-A and -B.

SYNTHESIS OF BOTH THE ENANTIOMERS OF HAUPTMANN'S PERIPLANONE-A AND CLARIFICATION OF THE STRUCTURE OF PERSOON'S PERIPLANONE-A

The naturally occuring (-)-enantiomer of Hauptmann's periplanone-A and its stereoisomers were synthesized.Thermal rearrangement of Hauptmann's (-)-periplanone A by GLC gave Persoon's periplanone-A, the structure of which was determined through an X-ray cr

IDENTIFIZIERUNG UND SYNTHESE VON PERIPLANON A

The pheromone periplanone-A has been isolated from fecal material of the female American cockroach (Periplaneta americana).The structure of periplanone-A was deduced spectroscopically and proved by its synthesis.