157192-67-1

Upstream product

• 24120-56-7 (E)-6,10-dimethyl-5,9-undecadienoic acid 
• 1666-13-3 diphenyl diselenide 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 24120-55-6 (E)-6,10-Dimethyl-5,9-undecadien-1-ol 
• 24120-53-4 2,6-Dimethyl-2,6-undecadiene-10-ene 

Relevant academic research and scientific papers

Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions

A range of substituted Se-phenyl 5,9-dieneselenoates, viz. 15a, 25, 26, 27, 42 and 52, have been synthesised and their reactions with Bu3SnH-AIBN investigated.The diene esters 15a, 42 and 52 are shown to lead to decalone and to perhydrophenanthrone derivatives, viz. 19, 43 and 53, respectively, via consecutive 6-endo trig modes of cyclisations starting from the corresponding 5,9-diene acyl radical intermediates.By contrast, the 5,9-dienoates 25 and 27 lacking alkyl substitution at C-9 instead underwent cyclisation to the indanones 36 and 37, respectively, and the 6-methyl substituted analogue 26 produced only the cyclopentanone 38 on treatment with Bu3SnH-AIBN.