TY - JOUR
T1 - Total synthesis of plakilactones C, B and des-hydroxyplakilactone B by the oxidative cleavage of gracilioether furanylidenes
AU - Norris, Matthew
AU - Perkins, Michael
PY - 2016/8/5
Y1 - 2016/8/5
N2 - A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4.
AB - A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4.
UR - http://www.scopus.com/inward/record.url?scp=84981278137&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b01196
DO - 10.1021/acs.joc.6b01196
M3 - Article
SN - 0022-3263
VL - 81
SP - 6848
EP - 6854
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -
