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A New Method for the Construction of Macrolides Stereoselective Synthesis of (±)-Phoracantholide J. Preliminary communication

✍ Scribed by Martin Petrzilka

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
249 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Starting from 5‐chloro‐2‐pentanone (1) the naturally occurring 10‐membered lactone phoracantholide J (8a) has been synthesized as its racemate in a sequence of six steps (Scheme 2). Salient features of the syntheis include an internal selenium assisted acetal formation (4→5) and a stereoselective Claisen rearrangement (6→7→8). This general synthetic strategy offers an alternative approach towards the construction of macrocyclic lactones.

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A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication
✍ Wolfgang Oppolzer; Fabrizio Marazza 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 212 KB

## Abstract The unusual propellane skeleton of the sesquiterpene modhephene (**1**) has been synthesized starting from cyclopentenone (**2**). The key step **6** → **7** is an efficient and highly stereoselective intramolecular thermal ene‐reaction. Further elaboration of the propellane **7** gave