𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The Effect of Sulfoxides on the Stereoselective Construction of Tetrahydrofurans: Total Synthesis of (+)-Goniothalesdiol

✍ Scribed by Dr. Gloria Hernández-Torres; Prof. Dr. M. Carmen Carreño; Dr. Antonio Urbano; Prof. Dr. Françoise Colobert

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
409 KB
Volume
17
Category
Article
ISSN
0947-6539

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Good to excellent stereoselectivities were achieved in the reductive cyclization (with Et~3~SiH/trimethylsilyl trifluoromethanesulfonate (TMSOTf)) of enantiopure hydroxy sulfinyl ketones en route to 2,5‐cis‐disubstituted tetrahydrofuran skeletons. Electrostatic effects of the exocyclic sulfoxide, which stabilized the reactive intermediate oxocarbenium conformations, were responsible for the observed stereocontrol. A model is proposed to explain the results. The use of this reaction and the asymmetric β‐ketosulfoxide reduction as key steps facilitated the total enantioselective synthesis of the natural β‐C‐aryl glycoside (+)‐goniothalesdiol.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of Agarof
ChemInform Abstract: Synthesis of Agarofuran Antifeedants. Part 2. Stereoselective Construction of the Tetrahydrofuran Ring.
✍ Francois-Didier Boyer; Paul-Henri Ducrot 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 26 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 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

Recent Advances in the Stereoselective S
Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans
✍ John P. Wolfe; Michael B. Hay 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 11 KB 👁 2 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, please click on HTML or PDF.