- Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations
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The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is
- Luo, Gan,Peng, Yu,Wang, Ya-Wen,Xiao, Jian,Zhao, Jun
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supporting information
p. 9840 - 9843
(2021/12/07)
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- Isotopically Sensitive Branching as a Tool for Evaluating Multiple Product Formation by Monoterpene Cyclases
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The deuterated substrates geranyl pyrophosphate and geranyl pyrophosphate were employed to examine isotopically sensitive branching in the biosynthesis of monoterpene olefin isomers.By this method, (-)-α-pinene and (-)-β-pinene were shown to be synthesized via a common intermediate by a single cyclization enzyme from grand fir (Abies grandis), as were (-)-α-phellandrene and (-)-β-phellandrene by a single cyclase from lodgepole pine (Pinus contorta).Kinetic isotope effects were determined for the various deprotonations leading to the pinenes and phellandrenes.Key Words: Isotopically sensitive branching, monoterpene biosynthesis, monoterpene cyclase, resin biosynthesis, kinetic isotope effect.
- Wagschal, Kurt,Savage, Thomas J.,Croteau, Rodney
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p. 5933 - 5944
(2007/10/02)
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- TRANSFORMATIONS OF p-MENTHADIENES UNDER THE ACTION OF POTASSIUM tert-BUTANOLATE IN DIMETHYL SULFOXIDE
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The products of the transformation of α- and γ-terpinenes, terpinolene, (+)-trans-isolimonene, and (+)-limonene under the action of potassium tert-butanolate in dimethyl sulfoxide contained - in addition to the α- and γ-terpinenes, isoterpinolene, p-mentha-3,8-diene and p-cymene found previously - terpinolene, α- and β-phellandrenes, p-mentha-2,4-diene (in total amount of 1-3percent), and polymers.Under these conditions, limonene is racemized.The primary products of the isomerization reaction have been identified.A supplementary scheme for the isomerization transformations of p-menthadienes is presented.
- Buinova, E. F.,Urbanovich, T. R.,Udarov, B. G.,Izotova, L. V.
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p. 555 - 559
(2007/10/02)
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