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4-Step Total Synthesis of (−)-Pavidolide B

preprint
submitted on 09.01.2020, 17:29 and posted on 13.01.2020, 21:01 by 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.

Funding

NIMHD 5G12MD007592

History

Email Address of Submitting Author

yzhu2@utep.edu

Institution

The University of Texas at El Paso

Country

United States

ORCID For Submitting Author

0000-0001-8988-9149

Declaration of Conflict of Interest

None

Exports