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.

Abstract

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.

• Authors: Karol Michalak, Michal Michalak, Jerzy Wicha
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 10 Issue 9 Pg. 1084-100 (Sep 30 2005) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 18007374 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Cyclooctanes
• Diterpenes
• Epoxy Compounds
• Glycosides
• Sesterterpenes
• ophiobolins
• fusicoccin
• cyclooctane

Topics

• Alkylation
• Cyclooctanes (chemistry)
• Diterpenes (chemical synthesis)
• Epoxy Compounds (chemistry)
• Glycosides (chemistry)
• Models, Molecular
• Sesterterpenes (biosynthesis, chemical synthesis, chemistry)