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

doi:10.3390/10091084

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Molecules 2005, 10(9), 1084-1100; doi:10.3390/10091084

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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

K. Michalak, M. Michalak and J. Wicha*

Institute of Organic Chemistry, Polish Academy of Sciences, Poland

* Author to whom correspondence should be addressed.

Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005

(This article belongs to the Special Issue Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”)

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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.

Keywords: Terpenes; total synthesis; cyclooctane derivatives; ring closing metathesis; Warner-Meerwein rearrangement.

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MDPI and ACS Style

Michalak, K.; Michalak, M.; Wicha, J. 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. Molecules 2005, 10, 1084-1100.

AMA Style

Michalak K, Michalak M, Wicha J. 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. Molecules. 2005; 10(9):1084-1100.

Chicago/Turabian Style

Michalak, K.; Michalak, M.; Wicha, J. 2005. "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." Molecules 10, no. 9: 1084-1100.

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