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2005
Terpenes
U 0200
11- 190
Diastereoselective Phenol para-Alkylation: Access to a Cross-Conjugated Cyclohexadienone en route to Resiniferatoxin. — A synthetic method leading to densely
functionalized spiro-fused cyclohexadienones through a novel series of transformations is described. Key step is the highly diastereoselective title reaction which affords
the desired spirocycle [cf. (V)] as a single diastereomer. In this way, a quaternary center
is created which is otherwise difficult to prepare. The combination of phenol alkylation
with the unexpected formation of a dioxepane-derived acetal opens a serviceable strategy. — (RITTER, T.; ZAROTTI, P.; CARREIRA*, E. M.; Org. Lett. 6 (2004) 23,
4371-4374; Lab. Org. Chem., ETH-Hoenggerberg, CH-8093 Zuerich, Switz.; Eng.)
— Steudel
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