A Quick Entry to the Aklavinone Ring System

In a clever, convergent and regiospecific route to the aklavinone ring system, it was shown that treatment of the lithio anion of the cyanophthalide 1 with the enone lactone 2 in THF/HMPA gave the tetracyclic quinone 3 directly (25% yield after conversion to the methyl ester and purification). 

It was reported that the structure of the product obtained (68% yield) by acid-catalysed (8% HC1, reflux, 18 hr) hydrolysis and decarboxylation of the (3-keto ester 1 was not the expected diketone, but the stable enol 2 (mp 128-130°C), and that the equilibrium could not be reversed from enol to ketone, even on treatment of 2 with dilute alkali for 10 days. The evidence cited in support of 2 was entirely spectroscopic, as follows C14H16O3 (232) M+ 232, Xmax (ethanol) 266 nm (log e, 4.09). The IR spectrum of 7 (= 2) showed a broad band between 3000-3500 cm 1 (enolic OH) and a sharp peak at 1705 cm-1 (ring -C=0) in the NMR spectrum (CDCI3) of 7 (s 2) a broad peak was present at 85.95 (1H, olefmic) and a downfield signal (exchangeable with D2O) at 811.1 (1H) indicating the presence of an enolic OH group.  

Assess this evidence in terms of structure 2, show that the claim to have prepared 2 as a stable enol is specious, and, on the basis of mechanism, devise a structure for the product from the acid-catalysed hydroysis of 1 (the molecular formula C14H16O3 for the product is correct). 

Conversion of an Indole-Based BicycIo[5.3.1]undecane into a Bicyclo[5.4.0]undecane 

Treatment of the product derived from reaction of the iV-oxide 1 with trifluoroacetic anhydride with sodium borohydride gives the tetracyclic indole derivative 2. 

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