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.
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.
Michalak
Karol
K
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warszawa, Poland.
Michalak
Michal
M
Wicha
Jerzy
J
D000478:Alkylation; D034242:Cyclooctanes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D008958:Models, Molecular; D054830:Sesterterpenes / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000737:chemistry
D034242:Cyclooctanes; D004224:Diterpenes; D004852:Epoxy Compounds; D006027:Glycosides; D054830:Sesterterpenes; C002884:ophiobolins; C007808:fusicoccin; C474479:cyclooctane