Hydroxy o-quinodimethanes

Table 5.1. Synthesis of tetralines by intermolecular trapping of hydroxy-o-quinodimethanes.

Nicolaou KC, Gray D, Tae J (2001) Total Synthesis of Hamigerans Part 2. Implementation of the Intramolecular Diels-Alder Trapping of Photochemically Generated Hydroxy-o-quinodimethanes Strategy and Completion of the Synthesis. Angew Chem Int Ed 40 3679... 

The photochemical generation of hydroxy-o-quinodimethanes from o-alkylbenz-aldehydes may be followed by a thermal Diels-Alder reaction with alkenes (Scheme 9.33) [54]. This reaction is effective in both intermolecular and intramolecular modes, and has been applied to the synthesis of various natural products [55],... 

Photolysis of orthotoluyl ketones has been utilized to generate the corresponding transient dienols (hydroxy o-quinodimethanes), which have been trapped by reaction with external or internal dienophiles. " ... 

Nicolaou KC, Gray DLF, Tae J (2003) Total synthesis of Hamigerans and analogues thereof. Photochemical generation and Diels-Alder trapping of hydroxy-o-quinodimethanes. J Am Chem Soc 126 613-627... 

Nicolaou, K.C., Gray, D., and Tae, J. (2001) Total synthesis of hamigerans Part 2. Implementation of the intramolecular Diels-Alder trapping of photochemically generated hydroxy-o-quinodimethanes strategy and completion of the synthesis. Angeut. Chem. Int. Ed., 40, 3679-3683. 

---