Total syntheses of polycyclic polyprenylated acylphloroglucinols Journal Article

  


Authors: Tsukano, C.; Siegel, D. R.; Danishefsky, S. J.
Article Title: Total syntheses of polycyclic polyprenylated acylphloroglucinols
Abstract: This review focuses on total syntheses of garsubellin A, nemorosone and clusianone, which are polycyclic polyprenylated acylphloroglucinols (PPAPs). The PPAPs feature a highly oxygenated and densely substituted bicyclo[3.3.1]nonane core with prenyl, geranyl, and acyl side chains, and exhibit a wide range of biological activity, including cytotoxicity, antibacterial activity, HIV inhibitory activity, and antioxidant activity etc. These compounds have attracted the considerable attention of organic chemists due to fascinating chemical structures and intriguing biological activities. For total synthesis of this class compounds, several strategies were established and employed to construct a bicyclo[3.3.1]nonane core. Shibasaki-Kanai utilized stereoselective intermolecular aldol reaction, Claisen rearrangement and ring-closing metathesis. Danishefsky employed dearomative allylation, iodocarbocyclization, and bridgehead functionalization reactions. Simpkins and Marazano-Delpech used a Claisen-Deieckmann reaction with malonyl chloride. Porco group employed a double Michael reaction approach.
Keywords: total synthesis; derivatives; core; garsubellin a; nemorosone; clusianone; polycyclic; polyprenylated acylphloroglucinols; bicyclo[3.3.1]nonane core; successive michael reactions; one-pot synthesis; garsubellin-a; vinyl; carbanions; natural-products; bicyclic system; floral resins; present; construction
Journal Title: Journal of Synthetic Organic Chemistry, Japan
Volume: 68
Issue: 6
ISSN: 0037-9980
Publisher: Society Synthetic Organic Chemistry Japan  
Date Published: 2010-06-01
Start Page: 592
End Page: 600
Language: Japanese
ACCESSION: ISI:000278900700002
PROVIDER: wos
Notes: --- - Review - "Source: Wos"