Stereocontrolled Synthesis and Reactions of Bicyclo[3.3.1]nonanes

Abstract

The stereocontrolled synthesis of bicyclo[3.3.1]nonanes, useful synthons and key structures of many natural compounds, is described. Functionalized derivatives of this framework are obtained by stereocontrolled cyclization reactions. Synthetic exploitation of chiral bicyclo[3.3.1]nonanes leading to enantiomers of bicyclic and polycyclic structures is demonstrated.

Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations

“…1 ) and have widespread applications in organic synthesis. 1 , 2 Although many creative approaches for the synthesis of these structures have been devised, 1 , 2 the preparation of enantiomerically enriched chiral bicyclo[3.n.1]alkanes by asymmetric catalysis currently represents only a small fraction of these methods. 3 , 4 In view of the present level of development, increasing the number of available catalytic enantioselective reactions to access these compounds is an important area of research.…”

The Chemistry of the Polycyclic Polyprenylated Acylphloroglucinols

“…A number of strategies developed for the construction of the bicyclo-[3.3.1]nonane system have been reported and reviewed by Peters, [4] and more recently by Butkus. [5] Although the work discussed therein largely focused on relatively unfunctionalized structures outside of the context of the PPAPs, it did provide some interesting insights concerning the foreseeable synthetic challenges. Ciochina and Grossman [1a] as well as Singh et al [1d] have independently also provided overviews on the early synthetic approaches towards the PPAPs.…”

Die Chemie der polycyclischen polyprenylierten Acylphloroglucine

“…[1a] Vom synthetischen Standpunkt aus gesehen ist es nicht überraschend, dass die vielversprechenden biologischen Profile der PPAPs, zusammen mit ihren herausfordernden Strukturen, großes Interesse an ihrer Synthese geweckt haben. Für die Konstruktion des Bicyclo[3.3.1]nonan-Systems wurden verschiedene Strategien beschrieben und sowohl von Peters [4] als auch erst kürzlich von Butkus [5] besprochen. Obwohl die dort diskutierten Arbeiten sich grçßtenteils auf relativ wenig funktionalisierte Strukturen außerhalb des Kontextes der PPAPs konzentrierten, lieferten sie einige interessante Einblicke in Bezug auf die vorhersehbaren Herausforderungen solcher Synthesen.…”