Total Synthesis of Salviachinensine A Using a Matteson Homologation Approach

被引：0

作者：

Kempf, Merlin ^{[1
]}

Andler, Oliver ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

[1] Saarland Univ, Organ Chem, Campus C4-2, DE-66123 Saarbrucken, Germany

来源：

HELVETICA CHIMICA ACTA | 2023年 / 106卷 / 10期

关键词：

boron; boronic esters; Chinese medicine; Matteson homologation; natural products; Friedel-Crafts alkylation; CHLORO BORONIC ESTERS; CHIRAL DIRECTOR; ACID; ZINC;

D O I：

10.1002/hlca.202300136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Salviachinensine A, a natural product obtained from the Chinese medicinal plant Salvia chinensis, was synthesized for the first time by employing Donald Matteson's boronic ester homologation. The use of (R,R)-dicyclohexylethane-1,2-diol (DICHED) enabled the generation of the required stereogenic centers in a highly stereoselective fashion. Salviachinensine A was formed in a one-pot protecting group cleavage/lactonization/ intramolecular Friedel-Crafts alkylation, followed by Lewis acid-catalysed cleavage of the acetal protecting groups. image

引用

页数：9

共 27 条

[1] Total synthesis of apratoxin A and B using Matteson's homologation approach
Andler, Oliver
Kazmaier, Uli
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) : 4866 - 4870
[2] Synthesis of Simplified Halogenated Chondramide Derivatives with Strong Cytostatic Properties
Becker, Dominic
Kazmaier, Uli
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (12) : 2591 - 2602
[3] Ambient-Pressure Asymmetric Preparation of S,S-DICHED, a C2-Symmetrical Director for Matteson Reactions
Bojaryn, Kevin
Hoffmann, Chris
Struth, Felix R.
Hirschhaeuser, Christoph
[J]. SYNLETT, 2018, 29 (08) : 1092 - 1094
[4] THE MECHANISM OF THE REACTION OF BORON TRICHLORIDE WITH CYCLIC ACETALS OF HEXITOLS
BONNER, TG
SAVILLE, NM
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (JUL): : 2851 - 2858
[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .16. BOROXAZOLIDONES DERIVED FROM ALPHA-AMINO-ACIDS AND BORINIC OR BORONIC ESTERS - A SIMPLE PROCEDURE FOR UPGRADING BORINATES AND BORONATES TO MATERIALS OF HIGH OPTICAL PURITY
BROWN, HC
GUPTA, AK
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) : 73 - 81
[6] (S)-(+)-N-acetylphenylglycineboronic acid:: A chiral derivatizing agent for Ee determination of 1,2-diols
Caselli, E
Danieli, C
Morandi, S
Bonfiglio, B
Forni, A
Prati, F
[J]. ORGANIC LETTERS, 2003, 5 (25) : 4863 - 4866
[7] Matteson Homologation-Based Total Synthesis of Lagunamide A
Gorges, Jan
Kazmaier, Uli
[J]. ORGANIC LETTERS, 2018, 20 (07) : 2033 - 2036
[8] Syntheses and anti-tubercular activity of -substituted and ,-disubstituted peptidyl -aminoboronates and boronic acids
Gorovoy, Alexey S.
Gozhina, Olga
Svendsen, John-Sigurd
Tetz, George V.
Domorad, Anna
Tetz, Victor V.
Lejon, Tore
[J]. JOURNAL OF PEPTIDE SCIENCE, 2013, 19 (10) : 613 - 618
[9] An efficient preparation of (R*,R*)-1,2-dicyclohexylethane-1,2-diol, a superior chiral director for synthesis with boronic esters
Hiscox, WC
Matteson, DS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8315 - 8316
[10] Synthesis of the cyclic heptapeptide core of callipeltin A
Horn, Alexander
Kazmaier, Uli
[J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5213 - 5218

← 1 2 3 →