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

Author: Michalak Karol   Michalak Michał   Wicha Jerzy  

Publisher: MDPI

E-ISSN: 1420-3049|10|9|1084-1100

ISSN: 1420-3049

Source: Molecules, Vol.10, Iss.9, 2005-09, pp. : 1084-1100

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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.