Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes

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

JOURNAL OF NATURAL PRODUCTS, vol.77, no.9, pp.2134-2137, 2014 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77 Issue: 9
  • Publication Date: 2014
  • Doi Number: 10.1021/np5001158
  • Journal Name: JOURNAL OF NATURAL PRODUCTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.2134-2137
  • Yozgat Bozok University Affiliated: No

Abstract

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).