Studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. Three-component approach to the A/B rings building block

• Published in: Molecules (Basel, Switzerland) Vol. 10; no. 9; pp. 1084 - 1100
• Main Authors: Michalak, Karol, Michalak, Michal, Wicha, Jerzy
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 30-09-2005; MDPI
• Subjects: Alkylation; Biological activity; Carbon; cyclooctane derivatives; Cyclooctanes - chemistry; Diterpenes - chemical synthesis; Epoxy Compounds - chemistry; Fungi; Glycosides - chemistry; Metabolites; Models, Molecular; ring closing metathesis; Sesterterpenes - biosynthesis; Sesterterpenes - chemical synthesis; Sesterterpenes - chemistry; Terpenes; total synthesis; Warner-Meerwein rearrangement
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/10091084

Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein rearrangement. Ring closing metathesis reaction leading to cyclopenta[8]annulene was studied in detail.