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The sequential annulation of an arene with a tetrahydrofuran provides a new route to the pseudopterosins

โœ Scribed by David C. Harrowven; Graham E.M. Sibley

Book ID
104262539
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
145 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The paper describes a new approach to the pseudopterosins i n which a sequential an%? alkylation with a tetrahydrofuran is used as a key step (viz. 2 + 1).

๐Ÿ“œ SIMILAR VOLUMES

A new approach to the pseudopterosins us
A new approach to the pseudopterosins using an arene alkylation with a ฮณ-methylene-ฮณ-butyrolactone
โœ David C Harrowven; Jonathan D Wilden; Melloney J Tyte; Michael B Hursthouse; Sim ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 87 KB

A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a g-methylene-g-butyrolactone, viz. 1014, and an elaborate reduction sequence 1417 which both proceed diastereoselectively.

The intramolecular alkylation of arenes
The intramolecular alkylation of arenes by higher cyclic ethers provides a stereoefficient route to tetralins
โœ David C. Harrowven; Richard F. Dainty ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 101 KB

Tetrahydrofurans and tetrahydropyrans tethered to arenes through a propyl chain readily undergo cyclisation to tetralins when exposed to titanium tetrachloride. The reaction has been shown to be highly stereospecific and an St,/2 type mechanism is implicated.