Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes

M. A. Gromova; Y. V. Kharitonov; T. V. Rybalova; E. E. Shul’ts

doi:10.1007/s10600-018-2327-x

Synthetic Transformations of Higher Terpenoids. 36.^* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes

M. A. Gromova, Y. V. Kharitonov, T. V. Rybalova, E. E. Shul’ts

New Functional Organic Materials Laboratory

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.

Original language	English
Pages (from-to)	293-300
Number of pages	8
Journal	Chemistry of Natural Compounds
Volume	54
Issue number	2
DOIs	https://doi.org/10.1007/s10600-018-2327-x
Publication status	Accepted/In press - 14 Apr 2018

Keywords

amino acids
isopimaric acid
Kornblum oxidation
oxazoles
Wacker oxidation
XSA
OXIDATION
NATURAL-PRODUCTS
STRATEGY
CRYSTAL-STRUCTURES
DITERPENOIDS
ISOPIMARIC ACID
DERIVATIVES
EFFICIENT

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title = "Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes",

abstract = "The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.",

keywords = "amino acids, isopimaric acid, Kornblum oxidation, oxazoles, Wacker oxidation, XSA, OXIDATION, NATURAL-PRODUCTS, STRATEGY, CRYSTAL-STRUCTURES, DITERPENOIDS, ISOPIMARIC ACID, DERIVATIVES, EFFICIENT",

author = "Gromova, {M. A.} and Kharitonov, {Y. V.} and Rybalova, {T. V.} and Shul{\textquoteright}ts, {E. E.}",

year = "2018",

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doi = "10.1007/s10600-018-2327-x",

language = "English",

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T1 - Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes

AU - Gromova, M. A.

AU - Kharitonov, Y. V.

AU - Rybalova, T. V.

AU - Shul’ts, E. E.

PY - 2018/4/14

Y1 - 2018/4/14

N2 - The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.

AB - The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.

KW - amino acids

KW - isopimaric acid

KW - Kornblum oxidation

KW - oxazoles

KW - Wacker oxidation

KW - XSA

KW - OXIDATION

KW - NATURAL-PRODUCTS

KW - STRATEGY

KW - CRYSTAL-STRUCTURES

KW - DITERPENOIDS

KW - ISOPIMARIC ACID

KW - DERIVATIVES

KW - EFFICIENT

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U2 - 10.1007/s10600-018-2327-x

DO - 10.1007/s10600-018-2327-x

M3 - Article

AN - SCOPUS:85045272459

VL - 54

SP - 293

EP - 300

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 2

ER -

Synthetic Transformations of Higher Terpenoids. 36.^* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes

Abstract

Keywords

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