140185-83-7

Upstream product

• 90-11-9 1-Bromonaphthalene 
• 6485-40-1 (R)-Carvone 
• 14474-59-0 naphthalen-1-yl-lithium 

Downstream Products

• 140185-87-1 (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one 
• 140185-84-8 (+)-(S)-5-<1-Bromo-2-methoxyprop-2-yl>-2-methyl-3-(1-naphthyl)cyclohex-2-en-1-one 

Relevant academic research and scientific papers

Radical Annulation Strategy to Chiral Pupukeanones: Total Synthesis of (+)-10-exo-(1-Naphthyl)pupukean-9-one and (+)-10-exo-(1-Naphthyl)-5-epipupukean-9-ones

Intramolecular alkylation reaction of the bromoenone 12, obtained from S-carvone in three steps, furnished the bicyclooctenone 13.Contrary to the anticipated radical annulation reaction, the bicyclic bromides 14 and 15, obtained from the enone 13, generated exclusively the cyclopropane product 18 via a 3-exo-trig radical cyclization on reaction with n-Bu3SnH and AIBN, even in the presence of a large excess of a radicophile.On the other hand, bromenone 24, synthesized from R-carvone via S-naphthylcarvone 21, underwent radical annulation reaction in the presence of radicophiles to furnish the isotwistanes 25-28 in a regio- and stereospecific manner.Hydrogenation of the olefin 34, obtained from the diketone 27 via a regiospecific Wittig reaction, furnished the naphthyl-5-epipupukean-9-one 33, whereas stereoselective hydrogenation of the enone 36, prepared from the keto ester 25 via a Grignard reaction and dehydration sequence, generated the naphthylpupukeanone 32.

A regio and stereospecific radical annulation route to chiral tricyclo[4.3.1.0]decane (isotwistane) system synthesis of (+)-10-α-naphthyl-5-epi-pupukean-9-one

Contrary to that of phanyl derivative 1 the radical 4 adds to radicophiles in an inter- followed by intra-molecular radical Michael addition (radical annulation), furnishing a novel route to chiral isotwistanes 5.