Enolic dienes, analysis

Ishikawa and coworkers reported a synthesis of ( )-0-methylkinamycin C (54) [32, 33]. Their retrosynthetic analysis is shown in Scheme 3.9. It was envisioned that 54 could be derived from the dihydroindanone 55 by D-ring oxygenation, installation of the diazo substituent, and oxidation of the protected hydroquinone function. The dihydroindanone 55 was envisioned to arise from the enol ether 56, itself formed from an endo Diels-Alder reaction between the indenone 59 and the diene 58. 

A nmr spectral analysis of the diene derivative from the reaction of complex 11 with the potassium enolate of acetone (in the presence of excess PPh3) showed it to have the structure 12. Thus, in common with... 

CHAllEHGtl Propose an efficient synthesis of the cyclohex-enol below, beginning exclusively with acychc starting materials and employing sound retrosynthetic analysis strategy. [Hint A Diels-Alder reaction may be useful, but take note of structural features in dienes and dienophiles that permit Diels-Alder reactions to work well (Section 14-8).]... 

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