2-Naphthoic acids aldehydes

Naphtoe-aldehyd, n. naphthaldehyde, naphthoic aldehyde, -skure, /. naphthoic acid. 

The aerobic reduction of aryl and alkyl carboxylates to the corresponding aldehydes. The reaction involves formation of an acyl-AMP intermediate by reaction of the carboxylic acid with ATP NADPH then reduces this to the aldehyde (Li and Rosazza 1998 He et al. 2004). The oxidoreductase from Nocardia sp. is able to accept a range of substituted benzoic acids, naphthoic acids, and a few heterocyclic carboxylic acids (Li and Rosazza 1997). 

Hofmann degradation, styrene 468 was formed. Epoxidation of 468 with m-chloroperbenzoic acid from the less hindered side and lithium aluminum hydride reduction gave ( )-epicorynoline (469). Moreover, slow addition of the a-methoxystyrene 471 to isoquinolinium salt 470 gave cycloadduct 472 in 90% yield. The adduct was hydrolyzed by acid and the resultant aldehyde oxidized to naphthoic acid by Jones oxidation. Modified Curtius rearrangement of 473 with added benzyl alcohol afforded benzyl urethane 474, which was reduced by lithium aluminum hydride and formylated with chloral to give 0-methylarnottiamide (475) (Scheme 60). 

Modifications to the Swem procedure often include a change of base from the requisite triethylamine. In their synthesis of naphthoic acid, Eustache and co-workers attempted to use Swem conditions to oxidise the 1,5-diol 11 to the corresponding dicarbonyl 12.10 Although evidence of the formation of the keto aldehyde intermediate was verified through H NMR, decomposition of the compound made further manipulations difficult. Eventually, a modified one-pot, two-step procedure was developed, involving oxidation followed by base-induced cyclisation to give the desired product. 

The polyphenolic binaphthyl gossypol 94 displays interesting pharmacological applications like male oral contraceptive, treatment of bronchitis, total inhibitor of HIV 1, and in vitro antiviral activity against herpes type 2 virus and influenza virus (Scheme 26.28). Apogossypol 95, a degradation derivative of gossypol that lacks the aldehyde functions, still has the potent pan-active inhibitor activity of antiapoptotic Bcl-2 family proteins. The naphthoic acid precursor can be obtained by... 

---