Evidence for pi-Stacking as a Source of Stereocontrol in the Synthesis of the Core Pyranochromene Ring System common to Calyxin I, Calyxin J, and Epicalyxin J

Cakir, SIDIKA; Stokes, Sean; Sygula, Andrzej; Mead, Keith

doi:10.1021/jo901436u

Evidence for pi-Stacking as a Source of Stereocontrol in the Synthesis of the Core Pyranochromene Ring System common to Calyxin I, Calyxin J, and Epicalyxin J

Cakir S., Stokes S., Sygula A., Mead K. T.

JOURNAL OF ORGANIC CHEMISTRY, cilt.74, sa.19, ss.7529-7532, 2009 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 74 Sayı: 19
Basım Tarihi: 2009
Doi Numarası: 10.1021/jo901436u
Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.7529-7532
Çanakkale Onsekiz Mart Üniversitesi Adresli: Hayır

Özet

A diastereoselective synthesis of the tetrahydropyrano-chromene ring system common to several natural product isolates of Alpinia blepharocalyx is reported. We have shown that a stereochemical preference exists for a syn configuration between the anomeric aryl substituents, representative of the C-7 and C-7' substituents in the natural products. Further, our results show that stereocontrol is under kinetic control, and calculations suggest that a favorable pi-stacking interaction may be the source of this stereocontrol.