Synthesis of some dihomodrimane and 14,15-dinorlabdane terpenoids with the amino-group

Kuchkova Kaleria; Aricu Aculina; Secara-Kușnir Elena; Barba Alic; Ungur Nikon; Vlad Pavel

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2021-04-07 09:17

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KUCHKOVA, Kaleria, ARICU, Aculina, SECARA-KUȘNIR, Elena, BARBA, Alic, UNGUR, Nikon, VLAD, Pavel. Synthesis of some dihomodrimane and 14,15-dinorlabdane terpenoids with the amino-group. In: The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova, 28-30 mai 2014, Chișinău. Chișinău, Republica Moldova: Institutul de Chimie al AȘM, 2014, p. 213.

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The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova 2014

Conferința "The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova"
Chișinău, Moldova, 28-30 mai 2014

Synthesis of some dihomodrimane and 14,15-dinorlabdane terpenoids with the amino-group

Pag. 213-213

Kuchkova Kaleria, Aricu Aculina, Secara-Kușnir Elena, Barba Alic, Ungur Nikon, Vlad Pavel

Institute of Chemistry of the Academy of Sciences of Moldova

Disponibil în IBN: 22 iunie 2020

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Rezumat

Many drimane sesquiterpenoids exhibit various types of biological activity [1]. In
continuation of our investigation on the synthesis of nitrogen containing drimane and
homodrimane sesquiterpenoids [2-5], we herein describe the synthesis of dihomordimane and
14,15-bis-norlabdane amines (4, 9, 10, 15) from commercially available norambreinolide (1) and
sclareol (11), according to the scheme given below.

Reagents and conditions: а. CH3Li, Et2O, 20°C, 15 min., 65%; b. NH2OH‧HCl, EtOH-Py (1:1), 20°C, 24 h, 97-
99%; c. LiAlH4, THF, 65°C, 10h, 53-58%; d. Аmberlyst-15, СН2Сl2, 20°C, 20h, a ratio of 5 and 6 (2.5 : 1), 95%. e.
KMnO4, CH3COCH3, 20°C, 5h, 60%; f. CH3SO3Si(СН3)3, CH3CN, 18°C, 10min, 96%; g. NH2OH‧HCl, EtOH-Py
(1:1), 20°C, 20h, 99%; h. LiAlH4, ТHF, Δ, 5h, 62%.
Reduction of the oximes (3, 7, 8, 14) with LiAlH4 in THF is considered as the key step. The
structure and stereochemistry of the newly obtained compounds were established on the basis of
their spectral data. The amines (4, 9, 10, 15) were synthesized in order to test their biological
activity.
References:
1. B.J.M. Jansen, A. De Groot, Nat. Prod. Rep , 2004, 21, 449.
2. K.I. Kuchkova, A.N. Arycu, P.F. Vlad, Chem. Nat. Comp., 2009, 45, 367.
3. K.I. Kuchkova, A.N. Arycu, P.F. Vlad, K. Deleanu, A. Nikolescu, Chem. Nat. Comp., 2010, 46, 539.
4. K.I. Kuchkova, A.N. Arycu, A.N. Barba, P.F. Vlad, Ya. Lipkovskii, Yu.A. Simonov, V.Kh. Kravtsov,
Chem. Nat. Comp., 2011, 47, 223.
5. K. Kuchkova, A. Aricu, A. Barba, P. Vlad, S. Shova, E. Secara, N. Ungur, G. Zbancioc, I.I. Mangalagiu,
Synlett, 2013, 24, 697.