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An Efficient Asymmetric Synthesis of Tarchonanthuslactone
Author(s) -
Enders Dieter,
Steinbusch Daniel
Publication year - 2003
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.200300412
Subject(s) - enantiopure drug , chemistry , umpolung , diastereomer , polyketide , lactone , ketone , enantioselective synthesis , yield (engineering) , enantiomeric excess , enantiomer , stereochemistry , organic chemistry , combinatorial chemistry , enzyme , catalysis , materials science , biosynthesis , metallurgy , nucleophile
An efficient and straightforward ten‐step asymmetric synthesis of the polyketide tarchonanthuslactone ( 1 ) in good overall yield (21% starting from chloro lactone 5 ) and with excellent diastereomeric and enantiomeric excesses ( de , ee ⩾ 96%) is described. The new synthetic route is based on the α,β‐unsaturated δ‐lactone building block 5 , available in enantiopure form ( ee > 99%) through an enzymatic procedure, and its conversion into methyl ketone 11 by an Umpolung strategy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)