57576-13-3Relevant articles and documents
Simple reagents for direct halonium-induced polyene cyclizations
Snyder, Scott A.,Treitler, Daniel S.,Brucks, Alexandria P.
scheme or table, p. 14303 - 14314 (2011/01/04)
Although there are many reagent combinations that can initiate polyene cyclizations, simple electrophilic halogen sources have not yet proven broadly effective as promoters of such processes. Herein is described a readily prepared and stable class of reagents capable of effecting such transformations for a wide range of electron-rich and -deficient terpenes derived from geraniol, farnesol, and nerol, thereby enabling the effective synthesis of a diverse array of complex chlorine-, bromine-, and iodine-containing polycyclic frameworks. Efforts to date have led to the first racemic laboratory total synthesis and structural revision of the anti-HIV natural product peyssonol A as well as an efficient and concise inaugural total synthesis of peyssonoic acid A. They have also permitted formal racemic total syntheses of aplysin-20, loliolide, K-76, and stemodin to be achieved through routes that are typically shorter, higher-yielding, and more environmentally conscious than previous efforts. Preliminary attempts to use chiral forms of the reagent class for enantioselective alkene halogenation are also described.
CATIONIC CYCLIZATION OF GERANONITRILE AND RELATED COMPOUNDS VIA THEIR BROMOHYDRINS: APPLICATION TO THE SYNTHESIS OF (+/-)-SNYDEROLS
Murai, Akio,Abiko, Atsushi,Kato, Koji,Masamune, Tadashi
, p. 1125 - 1128 (2007/10/02)
Cationic cyclization of bromohydrins of geranonitrile and homogeranonitrile in the presence of boron trifluoride complexes proceeded smoothly, giving mixtures of bromo cyclic olefins in satisfactory yields.This cyclization method was applied to the synthesis of (+/-)-snyderols.
