Total Synthesis of Peniphenones A–D via Biomimetic
Reactions of a Common <i>o</i>‑Quinone Methide Intermediate
Justin
T. J. Spence
Jonathan H. George
10.1021/acs.orglett.5b02902.s001
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_Peniphenones_A_D_via_Biomimetic_Reactions_of_a_Common_i_o_i_Quinone_Methide_Intermediate/2097568
The total synthesis of peniphenones
A–D has been achieved
via Michael reactions between appropriate nucleophiles and a common <i>o</i>-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.
2015-12-18 00:00:00
enantioselectively
methide
benzannulated spiroketal peniphenone
Peniphenone
Biomimetic Reactions
strategy
Michael reactions
synthesis
material
biosynthetic hypothesis
synthese
Common
nucleophile
Total Synthesis
IntermediateThe
Methide