(±)-Lingzhiol has been synthesized from commercially available 5,8-dimethoxytetralone in seven steps with an overall yield of 10.3% via an unprecedented acid-catalyzed semipinacol-type rearrangement. In addition, a novel strategy for the construction of the tetracyclic 5/5/6/6 core structure of lingzhiol has been developed via a tandem rearrangement/reduction/lactonization reaction.
A new approach for the synthesis of the (+)-conagenin has been achieved based on Evans asymmetry syn-aldol reaction and the self-regeneration of stereocenters strategy.
The relative and absolute configurations of xiamenmycin A, a benzopyran compound isolated from Streptomyces xiamenensis 318 with a highly potent anti-fibrotic activity, have been characterized through the total synthesis. The key steps include the construction of the 3-chromanol moiety via Sharpless epoxidation followed by regio- and diastereo-selective cyclization and introduction of the threonine moiety at a later stage via Pd-catalysed aminocarbonylation in a one-pot procedure. The stereochemical assignment of natural xiamenmycin A has been accordingly revised to be 2R, 3S, 3'S, 4'R.
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