𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The Biomimetic Synthesis and First Characterization of the (+)- and (−)-Isocentrolobines, 2,6-cis- and 2,6-trans-Disubstituted Tetrahydro-2H-pyrans

✍ Scribed by Frank Rogano; Georges Froidevaux; Peter Rüedi

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
512 KB
Volume
93
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The four stereoisomers of the novel title compounds were prepared by oxidative cyclization of their enantiomerically pure diarylheptanoid precursors by means of the straightforward biomimetic approach presented in the preceding article. The isocentrolobines are the methoxy regioisomers of the natural (+)‐ and (−)‐centrolobines and were characterized for the first time. The synthetic procedure established the absolute configurations and the unambiguous correlation with the chiroptical data. The spectroscopic and the chiroptical data of the isocentrolobines are highly similar to those of the natural products. The single diagnostic parameter that would allow a immediate assignment in the presence of only one of the isomers is the higher melting point (ca. 50°) of the __cis‐__configured isocentrolobines.

📜 SIMILAR VOLUMES

The Biomimetic Synthesis and Final Struc
The Biomimetic Synthesis and Final Structure Determination of (+)- and (−)-Centrolobine, Naturally Occurring Diarylheptanoid 2,6-cis-Disubstituted Tetrahydro-2H-pyrans
✍ Frank Rogano; Peter Rüedi 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 German ⚖ 444 KB

## Abstract The enantiomerically pure title compounds were prepared by oxidative cyclization of their optically active diarylheptanoid precursors. The approach is considered as a biomimetic phenol oxidation __via__ an intermediate quinone methide. The absolute configuration of the precursors is ret

ChemInform Abstract: InBr3-Catalyzed Ste
ChemInform Abstract: InBr3-Catalyzed Stereoselective Synthesis of trans-2,6-Disubstituted 3,6-Dihydro-2H-pyrans
✍ J. S. Yadav; V. Sunitha; B. V. Subba Reddy; P. P. Das; E. Gyanchander 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 24 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

The conformation of t-butyl 2-methoxy-5,
The conformation of t-butyl 2-methoxy-5, 6-dihydro-2 H-pyran-6-carboxylates and 6,6′- disubstituted 2-methoxy-5,6-dihydro-2H-pyran derivatives on the basis of 1H and 13 C NMR spectra
✍ Marek Chmielewski; Janusz Jurczak; Aleksander Zamojski; Halina Adamowicz 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 English ⚖ 474 KB

## Abstract The ^1^H and ^13^C NMR spectra of __trans__‐ and __cis__‐__tert__‐butyl 2‐methoxy‐5,6‐dihydro‐2__H__‐pyran‐6‐carboxylates (1 and 2) and 6,6′‐disubstituted 2‐methoxy‐5,6‐dihydro‐2__H__‐pyrans (3‐7) have been recorded. HH and CH coupling constants are discussed in terms of the ^1^H~6~⇄^6^