Pyrrolizidine Alkaloids by Intramolecular Palladium‐Catalysed Allylic Alkylation: Synthesis of (±)‐Isoretronecanol | Zendy

Lemaire Sébastien | Zendy; Giambastiani Giuliano | Zendy; Prestat Guillaume | Zendy; Poli Giovanni | Zendy

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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)

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