18296-18-9Relevant academic research and scientific papers
Synthesis of the Phytoalexin (+/-)-Phaseollin: 3-Phenylthiochromans as Masked 2H-Chromenes and o-Prenyl Phenols
Mohamed, Salah E. N.,Thomas, Philip,Whiting, Donald A.
, p. 431 - 438 (2007/10/02)
Phenylthiyl radicals are shown to add regiospecifically to 2H-chromenes to afford 3-phenylthiochromans (8), (10), (13), (14), and (15).The sulphide (15), as equivalent to a chromene protected against acid and oxidation, has been used in two syntheses of (+/-)-phaseollin, a major phytoalexin of beans and other legumes, via the sequence (17)->(18)->(19)->(20)->(21)->(+/-)-(1) or (19)->(22)->(23)->(+/-)-(1).Also the 3-phenylthiochromans, on electron transfer from metal naphthalenide or a mercury cathode, open to o-prenylphenols, providing a two step route to biogenetically important phenols from chromenes which is tolerant of free phenol and carbonyl functions and trisubstituted double bonds.
