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Pyrrolizidine Alkaloids by Intramolecular Palladium‐Catalysed Allylic Alkylation: Synthesis of (±)‐Isoretronecanol
Author(s) -
Lemaire Sébastien,
Giambastiani Giuliano,
Prestat Guillaume,
Poli Giovanni
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400135
Subject(s) - chemistry , intramolecular force , palladium , tsuji–trost reaction , pyrrolizidine , alkylation , yield (engineering) , allylic rearrangement , alkaloid , pyrrolizidine alkaloid , amination , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
An efficient and stereoconvergent approach to 3‐substituted hexahydroindol‐2‐one derivatives by palladium‐catalysed intramolecular allylic alkylation has been developed. Subsequently, the straightforward conversion of the hexahydroindol‐2‐one 7d into the alkaloid (±)‐isoretronecanol has been performed. The synthesis entails 11 steps starting from 1,3‐cyclohexadiene, affording the final target in a 29% overall yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)