Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes

Secinti H., BURMAOĞLU S., Altundas R., SEÇEN H.

JOURNAL OF NATURAL PRODUCTS, cilt.77, sa.9, ss.2134-2137, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 77 Sayı: 9
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1021/np5001158
  • Dergi Adı: JOURNAL OF NATURAL PRODUCTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2134-2137
  • Erzincan Binali Yıldırım Üniversitesi Adresli: Evet

Özet

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).