18278-24-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3007, 1984 DOI: 10.1016/S0040-4039(01)81350-2

Upstream product

• 201230-82-2 carbon monoxide 
• 612-17-9 1,4-dihydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 25108-63-8 1-methylene-1,2,3,4-tetrahydronaphthalene 
• 88533-92-0 (+/-)-trans-6-Bromo-6,7,8,9-tetrahydro-5-hydroxy-5H-benzocycloheptene 
• 53155-92-3 C₁₇H₂₃NO 
• 155566-54-4 1,2,3,4-tetrahydro-1-naphthalenecarbaldehyde 
• 85977-52-2 (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 447-53-0 1,2-Dihydronaphthalene 
• 17502-86-2 Methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 66377-63-7 (1,2,3,4-tetrahydronaphthalen-4-yl)methanol 
• 7125-62-4 1,2-benzo-1,3-cycloheptadiene 
• 93340-32-0 3,4-dihydro-1-naphthalenecarboxaldehyde 
• 53155-77-4 N-Cyclohexyl-α-chlor-δ-phenyl-valeraldonitron 

Downstream Products

• 66377-63-7 (1,2,3,4-tetrahydronaphthalen-4-yl)methanol 
• 25634-94-0 (1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanol 

Relevant academic research and scientific papers

Deracemization through photochemical E/Z isomerization of enamines

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Cobalt-Catalyzed Diborylation of 1,1-disubstituted Vinylarenes: A Practical Route to Branched gem-Bis(boryl)alkanes

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The full-structure of a norlabdane terpenoid, kujigamberol (1) was determined by total synthesis. Key features of the total synthesis are (1) installation of isopentyl group through an o-lithiation of benzamide, (2) construction of tetralone by the RCM reaction, and (3) optical resolution of (±)-1 using chromatographical separation of the corresponding camphanates. X-ray crystallographical analysis of p-bromobenzoate obtained from the more polar camphanate that was identical with a natural derivative, revealed natural kujigamberol to have an S-configuration. Both the natural enantiomer and its (R)-antipode showed the same inhibitory activity toward the mutant yeast and HL-60 cells, while simple analogs without alkyl groups at the C-8 and 9 positions of (±)-1 had no such activity.

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