studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. three-component approach to the ab rings building block研究对di -总合成和sesterterpenes dicyclopenta[a,d]环辛烷骨架。.pdfVIP

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studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. three-component approach to the ab rings building block研究对di -总合成和sesterterpenes dicyclopenta[a,d]环辛烷骨架。.pdf

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studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. three-component approach to the ab rings building block研究对di -总合成和sesterterpenes dicyclopenta[a,d]环辛烷骨架。

Molecules 2005, 10, 1084-1100 molecules ISSN 1420-3049 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 Karol Michalak, Michał Michalak and Jerzy Wicha* Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warszawa, Poland; * Author to whom correspondence should be addressed; E-mail: jwicha@.pl Received: 23 April 2005 / Published: 30 September 2005 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. Keywords: Terpenes, total synthesis, cyclooctane derivatives, ring closing metathesis, Warner-Meerwein rearrangement. Introduction Ophiobolin A (Scheme 1) has been identified in the 1960s as a metabolite of the fungus Helminthsporium oryzeo , toxic to rice seedlings [1]. A number of related sesterterpenoids have been isolated since then from terrestrial and marine microorganisms, plants and insect se