Article

Phytochemistry Reviews

, Volume 12, Issue 1, pp 95-105

Cubitane: a rare diterpenoid skeleton

  • Johannes WeferAffiliated withInstitute of Organic Chemistry, Technische Universität Braunschweig
  • , Kristina SimonAffiliated withInstitute of Organic Chemistry, Technische Universität Braunschweig
  • , Thomas LindelAffiliated withInstitute of Organic Chemistry, Technische Universität Braunschweig Email author 

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Abstract

There are only 15 diterpenoids known sharing the rare cubitane skeleton (1,3-diisopropyl-6,10-dimethylcyclododecane, Fig. 1) named after the natural product (+)-cubitene ((+)-1) from the termite Cubitermes umbratus. Cubitane-type diterpenoids (“cubitanoids”) have since then been isolated from gorgonian corals and there are reports that cubitene also occurs in plants. The twelve-membered ring of the cubitanoids is an interesting feature for which we have developed a novel synthesis involving bicyclic precursors. In this review, we discuss the state-of-research regarding isolation, structure elucidation, biological activity, biosynthesis, and total synthesis of cubitane-type diterpenoids.
http://static-content.springer.com/image/art%3A10.1007%2Fs11101-012-9257-1/MediaObjects/11101_2012_9257_Fig1_HTML.gif
Fig. 1

Cubitane skeleton and cubitanoids from termites

Keywords

Diterpenoids Total synthesis Structure elucidation Cubitane