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Total Synthesis of (±)‐Decursivine
Author(s) -
Leduc Andrew B.,
Kerr Michael A.
Publication year - 2007
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.200600922
Subject(s) - chemistry , aldol reaction , natural product , adduct , total synthesis , substrate (aquarium) , organic chemistry , indole test , boron , borylation , aldol condensation , combinatorial chemistry , stereochemistry , catalysis , oceanography , alkyl , aryl , geology
The first preparation of the antimalarial natural product decursivine is described. A Diels–Alder/Plieninger indolization protocol allows convenient preparation of the indole 15 which, in turn is a suitable substrate for a boron–enolate aldol reaction with piperonal ( 16 ). The resulting adduct 14 is transformed efficiently to the natural product. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)