Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes

Bredenkoetter B, Neumann B, Stammler H-G, Kuck D (2014)
European Journal of Organic Chemistry 2014(1): 53-65.

Journal Article | Published | English

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Abstract
The construction of the polycyclic frameworks of phenanthro-annelated all-cis-[5.5.6.6]fenestrane, cis,cis,trans,cis-[5.5.6.6]fenestrane, and a related broken [6.5.6]fenestrane is reported for the first time. On the basis of our established synthesis of benzoannelated fenestrindanes, spirocyclic di(9-phenanthryl)methyl-1,3-indanediols were prepared with complete stereocontrol and subjected to cyclodehydration. Surprisingly, the 9-phenanthrylmethyl residues underwent preferential peri attack, rather than ortho attack, to generate 1,10-phenanthro rather than 9,10-phenanthro units. In this way, the cyclodehydration of 2,2-di(9-phenanthryl)methyl-1,3-indanediol gives rise to two new six-membered rings with the [6.5.6]fenestrane skeleton. The cyclodehydration of the related trans- and cis-diphenanthryl spiro(cyclohexane-1,2-indanediols) generated one new five- and one new six-membered ring stereospecifically to afford the respective all-cis- and cis,cis,trans,cis-benzodiphenanthro[5.5.6.6]fenestranes in good yields. The crucial constitutional and stereochemical features of the new fenestranes were determined by single-crystal X-ray structure analysis and variable-temperature (VT) NMR spectroscopy.
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Bredenkoetter B, Neumann B, Stammler H-G, Kuck D. Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes. European Journal of Organic Chemistry. 2014;2014(1):53-65.
Bredenkoetter, B., Neumann, B., Stammler, H. - G., & Kuck, D. (2014). Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes. European Journal of Organic Chemistry, 2014(1), 53-65.
Bredenkoetter, B., Neumann, B., Stammler, H. - G., and Kuck, D. (2014). Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes. European Journal of Organic Chemistry 2014, 53-65.
Bredenkoetter, B., et al., 2014. Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes. European Journal of Organic Chemistry, 2014(1), p 53-65.
B. Bredenkoetter, et al., “Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes”, European Journal of Organic Chemistry, vol. 2014, 2014, pp. 53-65.
Bredenkoetter, B., Neumann, B., Stammler, H.-G., Kuck, D.: Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes. European Journal of Organic Chemistry. 2014, 53-65 (2014).
Bredenkoetter, Bjoern, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes”. European Journal of Organic Chemistry 2014.1 (2014): 53-65.
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