ol5b02902_si_001.pdf (4.59 MB)
Total Synthesis of Peniphenones A–D via Biomimetic Reactions of a Common o‑Quinone Methide Intermediate
journal contribution
posted on 2015-12-18, 00:00 authored by Justin
T. J. Spence, Jonathan H. GeorgeThe total synthesis of peniphenones
A–D has been achieved
via Michael reactions between appropriate nucleophiles and a common o-quinone methide intermediate. This strategy, which was
based on a biosynthetic hypothesis, minimized the use of protecting
groups and thus facilitated concise syntheses of the natural products.
The most complex target, the benzannulated spiroketal peniphenone
A, was synthesized enantioselectively in nine linear steps from commercially
available starting materials.