A vicarious one-pot transformation of a fluorocyclitol to a polycyclitol: observation of a formal 4-fold axial-equatorial epimerization on a conformationally locked scaffold.
A conformationally locked fluoropentol undergoes an interesting transformation to (trans,anti,trans,anti,trans)-perhydro-2,3,4a,6,7,8a-naphthalenehexol essentially under conditions of base-induced transesterification. The proposed rationale for the observed metamorphosis involves a nucleophilic displacement of fluoride, and subsequent stereo- and regioselective anti-Fürst-Plattner-type ring-opening of the epoxide thus formed.
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. gmsc@uohyd.ernet.in
Goverdhan
G
Mehta
Saikat
S
Sen