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The Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one via Prins Cyclization

✍ Scribed by Jhillu Singh Yadav; Dandekar Chandrakanth; Yerragorla Gopala Rao; Kontham Ravindar; Basi V. Subba Reddy

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

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✦ Synopsis

Abstract

The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural product (6__S__)‐5,6‐dihydro‐6‐[(2__R__)‐2‐hydroxy‐6‐phenylhexyl]‐2__H__‐pyran‐2‐one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring‐closing metathesis reaction.

📜 SIMILAR VOLUMES

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^