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Stereoselective total syntheses of (±)-chanoclavine I and (±)-isochanoclavine I by an intramolecular nitrone-olefin/cycloaddition. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; J. Ian Grayson

Publisher: John Wiley and Sons
Year: 1980
Tongue: German
Weight: 256 KB
Volume: 63
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19800630639

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✦ Synopsis

Abstract

The racemic alkaloids chanoclavine I (1) and isochanoclavine I (2) have been synthesized stereoselectively from indole‐4‐carbaldehyde (3) by a sequence of 11 operations in overall yields of 14% and 2.4%, respectively. The key step 6 → 8 (Scheme 2) involves a transient nitrone 7 which undergoes a regio‐ and stereoselective intramolecular cycloaddition to a 1,2‐disubstituted olefinic bond.

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A Highly Stereoselective Synthesis of C(11)-Functionalized Aromatic Steroids by an Intramolecular Benzocyclobutene-Olefin -Cycloaddition. Preliminary Communication

✍ Wolfgang Oppolzer; Martin Petrzilka; Kurt Bättig 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 246 KB

## Abstract The racemic __cis__‐__anti__‐__trans__‐steroids **9** to **11** have been synthesized in a highly stereoselective manner starting from 4‐methoxybenzocyclobutene carboxylic acid __via__ the key step **8** → **9**. (__cf. Scheme 2__).