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Synthesis of the Tetraketide Lactones from the Pikromycin Biosynthetic Pathway
Author(s) -
Oh HongSe,
Yun JiSuk,
Nah KiHyun,
Kang HanYoung,
Sherman David H.
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.200700254
Subject(s) - chemistry , lactone , polyketide , reformatsky reaction , aldol reaction , stereochemistry , total synthesis , ring (chemistry) , enantioselective synthesis , bicyclic molecule , biosynthesis , organic chemistry , catalysis , enzyme
Synthesis of tetraketide lactones 2 and 3 , which are likely to be produced by a model pikromycin polyketide synthase (PKS), has been investigated. The tetraketide lactones with six‐membered rings, 2a and 2b , were synthesized successfully by the asymmetric aldol reaction, allylation, and the Reformatsky reaction. The attempted synthesis of tetraketide lactones with eight‐membered rings, 3a and 3b , led to the formation of the compounds 2a and 2b . The synthesis of another tetraketide lactone compounds 35 was attempted with the hope that introducing an additional methyl group would lead to a change in thermodynamic stability. However, it produced the corresponding tetraketide lactone 34 with a six‐membered ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)