Stereodivergent Strategy in Structural Determination: Asymmetric Total Synthesis of Garcinol, Cambogin, and Related Analogues
Xueying Wang, Yee Lin Phang, Jiling Feng, Song Liu, Hong Zhang, Wenwei Fu, Hua Zhou, Gang Xu, Hong‐Xi Xu, Changwu Zheng
Abstract
The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. Along the way, an efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.
Topics & Concepts
ChemistryStereocenterDiastereomerNonaneStereochemistryTotal synthesisEnantioselective synthesisSequence (biology)Ring (chemistry)Combinatorial chemistryOrganic chemistryCatalysisBiochemistryNatural Compound Pharmacology StudiesCarbohydrate Chemistry and SynthesisSynthesis of Organic Compounds