Synthesis of polyoxygenated dibenzo[ a , e ]cycloheptatrienes

Chan, Chieh‐Kai; Chan, Yi-Ling; Tsai, Yu‐Lin; Chang, Meng‐Yang

doi:10.1016/j.tet.2017.02.054

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“…Oxygenated 2-allylbenzaldehydes 3 were synthesized easily from commercially available isovanillin and 3-hydroxybenzaldehyde via a three-step synthetic route (O-allylation, Claisen rearrangement, O-alkylation) according to our previous reports. [23][24][25][26][27][28][29][30][31] Scheme 2 Synthetic route to the starting materials 1…”

Section: Syn Thesismentioning

confidence: 99%

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

2019

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A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH4-mediated reduction of oxygenated o-allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible mechanism is proposed and discussed. This protocol provides highly effective regio- and stereocontrolled allyl-enone cross-coupling to construct two stereocenters and one E-configured styryl group.

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