Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes

Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes

The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicauli...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2014-09, Vol.77 (9), p.2134-2137
Hauptverfasser: Seçinti, Hatice, Burmaoğlu, Serdar, Altundaş, Ramazan, Seçen, Hasan
Format: Artikel
Sprache:eng
Schlagworte:
Benzaldehydes - chemistry
Cyclization
Molecular Structure
Organophosphorus Compounds - chemistry
Oxidation-Reduction
Phenanthrenes - chemical synthesis
Phenanthrenes - chemistry
Stilbenes - chemistry
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Zusammenfassung:The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
ISSN:0163-3864
1520-6025
DOI:10.1021/np5001158