112709-50-9

Upstream product

• 69239-67-4 Persoon's periplanone-A 
• 131548-66-8 (1S*,2R*,6R*,7R*,8R*,10S*)-6-Acetoxy-8-tert-butyldimethylsilyloxy-10-isopropyl-11-oxatricyclo<5,3,2,0^2,7>-3-dodecanone 
• 127940-64-1 (1S,4R,4aS,8aR)-4-(1-Ethoxy-ethoxy)-1-hydroxy-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 
• 127940-47-0 (4R*,4aS*,8aR*)-4,4a,5,8-Tetrahydro-4-hydroxy-4a-methoxycarbonyl-1(8aH)-naphthalenone 
• 127940-61-8 Methanesulfonic acid (1S,4R,4aR,8aR)-1,4-bis-(1-ethoxy-ethoxy)-1,5,8,8a-tetrahydro-4H-naphthalen-4a-ylmethyl ester 
• 127940-65-2 (1S*,4R*,4aR*,8aR*)-1,4-Bis-(1-ethoxy)ethoxy-1,4,4a,5,8,8a-hexahydro-4a-methoxycarbonylnaphthalene 
• 127940-56-1 C₂₀H₃₄O₄Si 
• 127940-58-3 (1S*,2R*,6R*,7R*,8R*,10S*)-8-tert-Butyldimethylsilyloxy-6-hydroxy-10-isopropyl-11-oxatricyclo<5,3,2,0^2,7>-4-dodecen-3-one 
• 127940-57-2 (1R*,2R*,5S*,6S*,7S*,8S*,10R*)-10-tert-Butyldimethylsilyloxy-8-isopropyl-11-oxatricyclo<5,3,2,0^1,6>-3-dodecene-2,5-diol 
• 127940-60-7 (1S*,2R*,6R*,7R*,8R*,10S*)-8-tert-Butyldimethylsilyloxy-6-hydroxy-10-isopropyl-11-oxatricyclo<5,3,2,0^2,7>-3-dodecanone 
• 127970-23-4 (1R*,2R*,6R*,7S*,8S*,10R*)-10-tert-butyldimethylsilyloxy-8-isopropyl-5-methylene-11-oxatricyclo<5,3,2,0^1,6>-2-dodecanol 
• 111537-75-8 (1S*,2R*,7R*,8R*,10S*)-8-tert-butyldimethylsilyloxy-10-isopropyl-3-methylene-11-oxatricyclo<5,3,2,0^2,7>-5-dodecene 
• 127940-54-9 tert-Butyl-((1R,6R,7S,8S,10R)-8-isopropyl-12-oxa-tricyclo[5.3.2.0^1,6]dodeca-2,4-dien-10-yloxy)-dimethyl-silane 
• 127940-63-0 (4R*,4aS*,8aR*)-4-(1-Ethoxy)ethoxy-4,4a,5,8-tetrahydro-4a-methoxycarbonyl-1(8aH)-naphthalenone 

Downstream Products

• 69239-67-4 (1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one 

Relevant academic research and scientific papers

Synthesis of (+-)-PA 22-VII, the racemate of the rearrangement product of Persoons's periplanone-A

A synthesis of the racemate of 5 was achieved to prove its identity with PA 22-VII, the stable and biologically inactive rearrangement product of Persoons's periplanone-A.

SYNTHETIC CONFIRMATION OF THE STRUCTURE OF THE REARRANGEMENT PRODUCT OF PERIPLANONE-A

The stable and biologically inactive rearrangement product of Persoons's periplanone-A was shown to be 12 by the synthesis of (+/-)-12

CLARIFICATION OF THE STRUCTURE OF PERSOONS'S PERIPLANONE-A, AN ARTIFACT DERIVED FROM HAUPTMANN'S PERIPLANONE-A

Thermal rearrangement of Hauptmann's periplanone-A by GLC gave Persoons's periplanone-A, of which structure was determined through an X-ray crystallographic analysis of the corresponding alcohol.

WHAT IS THE CORRECT STRUCTURE FOR PERIPLANONE A?

The stereostructures of periplanone A and its rearrangement product have been elucidated on the basis of molecular mechanics calculations together with 1H NMR spectral data.