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Addition of Indole to Methyl 2-Chloro-2-cyclopropylideneacetate en Route to Spirocyclopropanated Analogues of Demethoxyfumitremorgine C and Tadalafil

✍ Scribed by Michael Limbach; Suryakanta Dalai; André Janssen; Mazen Es-Sayed; Jörg Magull; Armin de Meijere

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
189 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Indole readily added across the double bond of the highly reactive Michael acceptor methyl 2‐chloro‐2‐cyclopropylideneacetate (4) to yield 2‐chloro‐2‐(3′‐indolylcyclopropyl)acetate 5 (85%) which was converted in two steps into the racemic tryptophan analogue 7 in 90% yield. This in turn was transformed by a condensation and Pictet−Spengler sequence into the spirocyclopropane analogues, 11, 13 and 15, of both the natural product (demethoxy)fumitremorgine C (3b, 3 steps, 11% yield) and the potent PDE‐5 inhibitor Tadalafil (2, 3 steps, 71% yield) as well as the original lead structure with a hydantoin backbone (1, 2 steps, 79% yield). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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