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Synthesis of the microbial elicitor syringolide 2 multiply labelled with deuterium
Author(s) -
Henschke Julian P.,
Rickards Rodney W.
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199803)41:3<211::aid-jlcr69>3.0.co;2-9
Subject(s) - chemistry , elicitor , acylation , deuterium , tritium , side chain , chemical synthesis , total synthesis , organic chemistry , derivative (finance) , catalysis , stereochemistry , combinatorial chemistry , biochemistry , enzyme , physics , polymer , quantum mechanics , nuclear physics , financial economics , economics , in vitro
Deuterated syringolide 2 3 was prepared from D‐xylulose and 8‐bromooctanoic acid by a convergent route based on our previously reported biomimetic synthesis of this microbial elicitor. Key steps were the thermal acylation of the anisylidene‐protected sugar 6 with the C‐octenoyl Meldrum's acid derivative 7b , the one‐pot triple‐cyclisation of the xylulose β‐ketoester 9b to 9,10‐dehydrosyringolide 2 ( 10 ), and the introduction of multiple deuterium labels in the side chain by catalytic exchange and reduction. The route is applicable to the synthesis of tritium labelled syringolide 2 4 . © 1998 John Wiley & Sons, Ltd.