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Download fileSynthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate
journal contribution
posted on 2017-11-27, 00:00 authored by Michael
C. Dieckmann, Pierre-Yves Dakas, Alain De MesmaekerStrigolactones
are plant hormones regulating essential stages of
a plant’s development. Their low natural abundance combined
with a low chemical stability significantly hampered the detailed
investigation of their biological activity. Noncanonical strigolactones
lack the fused tricyclic ABC-ring system commonly present in canonical-type
strigolactones but feature an open-chain unit linking structurally
diverse A-ring moieties to the butenolide D-ring. We herein present
an efficient synthetic access to enantiomerically pure noncanonical
strigolactones by a Stille cross-coupling approach to forge the central
diene moiety and demonstrate this strategy by syntheses of natural
products methyl carlactonoate and carlactonic acid. Furthermore, a
synthetic access to deuterium-labeled analogues of these natural products
has been developed.
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Synthetic Accesscanonical-type strigolactonescarlactonic acidA-ring moietiesdeuterium-labeled analoguestricyclic ABC-ring systemNoncanonical StrigolactonesMethyl Carlactonoate Strigolactoneschemical stabilityplant hormonesdiene moietyNoncanonical strigolactones lackStille cross-coupling approachproducts methyl carlactonoateopen-chain unitbutenolide D-ringaccessnoncanonical strigolactones