In:
Helvetica Chimica Acta, Wiley, Vol. 74, No. 2 ( 1991-03-13), p. 275-289
Abstract:
The imine obtained by condensing indole‐protected 2‐(indol‐3‐yl)acetaldehyde ( 5 ) with the terpinylamine derivative (±)‐ 4 was cyclized in 51% yield to the 19‐substituted hobartine derivative (±)‐ 20 upon exposure to anhydrous HCOOH. This pivotal intermediate was further elaborated into the indole alkaloids (±)‐serratenone ((±)‐ 22 ) and (±)‐sorelline ((±)‐ 29 ). In the course of these investigations, a novel rearrangement was uncovered; a Lewis acid‐catalyzed 1,3‐migration of an arylsulfonyl group from the indole N‐atom into the benzene ring. The discovery that synthetic (±)‐aristotelin‐19‐one ((±)‐ 34 ) has decidedly different spectroscopic properties than aristolasicone, a metabolite for which the structure has been recently proposed, led to a revision of the structure of the latter.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19910740204
Language:
English
Publisher:
Wiley
Publication Date:
1991
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
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