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submitted on 09.01.2020 and posted on 13.01.2020by Yaoqiu Zhu, Elkin L. Romero, Kolluru Srinivas, Elizabeth Noriega
(−)-Pavidolide B is a complex
tetracyclic diterpenoid with seven contiguous stereocenters, and classical
total syntheses have recently been reported. In this work, an annulation strategy
of carbanion cascade reaction is formulated for accomplishing an asymmetric
total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction
is a tandem intramolecular Michael addition, which constructs two 5-membered
rings and five stereocenters in a highly selective fashion in one step. This
work represents one of the most efficient cases of total synthesis and
demonstrates that synthetic access to complex therapeutic natural product can
be greatly simplified.