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Total Synthesis of Altenuene and Isoaltenuene
Author(s) -
Altemöller Martina,
Podlech Joachim,
Fenske Dieter
Publication year - 2006
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.200500904
Subject(s) - chemistry , quinic acid , total synthesis , acetal , palladium , sequence (biology) , stereochemistry , organic chemistry , catalysis , biochemistry
Abstract Total synthesis of altenuene and isoaltenuene, toxins produced by various alternaria fungi, were achieved for the first time in ten steps, starting with quinic acid and commercially available acetal‐protected phloroglucinic acid, with the longest linear sequence consisting of seven steps. The key reactions are palladium‐catalyzed Suzuki‐type couplings between an arene boronate and iodinated cyclohexenes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)