Synthesis of the Natural Coumarin Products Murraol and （E）-Suberenol
Liu Zhiwen1, 2, Gong Xushun1, 2, Zhang Kai1, 2, Lei Ting1, 2, Jiang Shizhi1, 2*
（1. College of Pharmacy, Dali University, Dali, Yunnan 671000, China; 2. Yunnan Key Laboratory of Screening and
Research on Anti-pathogenic Plant Resources from Western Yunnan, Dali, Yunnan 671000, China）
Liu Zhiwen, , Gong Xushun, , Zhang Kai, , Lei Ting, , Jiang Shizhi, . Synthesis of the Natural Coumarin Products Murraol and （E）-Suberenol[J]. Journal of Dali University, 2024, 9(8): 14-19.
〔1〕 MURRAY R D H. The Naturally Occurring Coumarins〔J〕.
Fortschr Chem Org Naturst，1978，35：199.
〔2〕 SANTOS C M，CARDOSO S M，SALES E M，et al. Couma⁃
rins from Rutaceae：Chemical Diversity and Biological Ac⁃
tivities〔J〕. Fitoterapia，2023，168：105489.
〔3〕 TU Y B，YANG Y，LI Y F. Naturally Occurring Coumestans
from Plants，Their Biological Activities and Therapeutic Ef⁃
fects on Human Diseases〔J〕. Pharmacol Res，2021，169：
105615.
〔4〕 FURUKAWA H，ITO C. Three New Coumarins from Mur⁃
raya exotica〔J〕. Heterocycles，1987，26（7）：1731.
〔5〕 GUISE G B，RITCHIE E，SENIOR R G，et al. The Chemi⁃
cal Constituents of Australian Zanthoxylum Species. IV.
Two New Coumarins from Z. suberosum C. T. White （syn.
Z. dominianum Merr. & Perry；Z. ovalifolium Wight）〔J〕.
Aust J Chem，1967，20（11）：2429-2439.
〔6〕 BRYCE T A，WELTI D，WALSBY A E，et al. Monohexo⁃
side Derivatives of Long-Chain Polyhydroxy Alcohols；A
Novel Class of Glycolipid Specific to Heterocystous Al⁃
gae〔J〕. Phytochemistry，1972，11（1）：295-302.
〔7〕 BANDARA B M R，GUNATILAKA A A L，WIJERATNE E
M K，et al. Acridone Alkaloids and Coumarins from Pleio⁃
spermium alatum〔J〕. Phytochemistry，1990，29（1）：297-
301.
〔8〕PAN S. Evaluation of Emulsifiable Concentrate and Wet⁃
table Power Insecticides for Control of Rice Tungro Virus-
Disease and Its Vector〔J〕. Phattacharyya，Pjlanzenkr.
Pjlanzenschutz，1983，90（3）：269-277.
〔9〕 RAJ K，KAPIL R S，POPLI S P. ChemInform Abstract：Syn⁃
thesis of Suberenol and Coumarin RR8〔J〕. ChemInform，
1975，6（29）：269.
〔10〕 SCHOENBERG A，BARTOLETTI I，HECK R F. Palladium-
Catalyzed Carboalkoxylation of Aryl，Benzyl，and Vinylic
Halides〔J〕. J Org Chem，1974，39（23）：3318-3326.
〔11〕 MURRAY R D H，ZEGHDI S. Synthesis of the Natural
Coumarins，Murraol （CM-c2），Trans-Dehydroosthol and
Switenocoumarin G〔J〕. Phytochemistry，1989，28（1）：
227-230.
〔12〕 FURUKAWA H，ITO C，MIZUNO T，et al. Spectrometric
Elucidation of Acrimarines，the First Naturally Occurring
Acridone-Coumarin Dimers〔J〕. J Chem Soc Perkin Trans
1，1990，21（6）：1593-1599.
〔13〕 CAIRNS N，HARWOOD L M，ASTLES D P. Synthesis of
Linear Coumarins via Para-Claisen Rearrangement of
Coumarate Ester Derivatives：Total Synthesis of Suberosin，
Demethylsuberosin，and Ostruthin〔J〕. J Chem Soc，
1986，16：1264-1266.
〔14〕 GUTHERTZ A，LEUTZSCH M，WOLF L M，et al. Half-
Sandwich Ruthenium Carbene Complexes Link Trans-
Hydrogenation and Gem-Hydrogenation of Internal Al⁃
kynes〔J〕. J Am Chem Soc，2018，140（8）：3156-3169.
〔15〕 GONG X S，BAI M J，LU G D，et al. Total Synthesis of
Murraol，（E）-Suberenol and toward the Collective Total
Synthesis of Exotines A，Cnidimonins A-Cetc〔J〕. Tetra⁃
hedron，2022，126：133061.
〔16〕BHARATHI M V，CHHABRA M，PAIRA P. Development
of Surface Immobilized 3-Azidocoumarin-Based Fluoro⁃
genic Probe via Strain Promoted Click Chemistry〔J〕.
Bioorg Med Chem Lett，2015，25（24）：5737-5742.
〔17〕KHAN D ，MUKHTAR S ，ALSHARIF M A ，et al.
PhI（OAc）2 Mediated an Efficient Knoevenagel Reaction
and Their Synthetic Application for Coumarin Deriva⁃
tives〔J〕. Tetrahedron Lett，2017，58（32）：3183-3187.
〔18〕 SHAKIL M R，MEGUERDICHIAN A G，TASNIM H，et al.
Syntheses of ZnO with Different Morphologies：Catalytic
Activity toward Coumarin Synthesis via the Knoevenagel
Condensation Reaction〔J〕. Inorg Chem，2019，58（9）：
5703-5714.
〔19〕 SAMADIZADEH M，NOURI S，MOGHADAM F K. Mag⁃
netic Nanoparticles Functionalized Ethane Sulfonic Acid
（MNESA）：As an Efficient Catalyst in the Synthesis of
Coumarin Derivatives Using Pechmann Condensation un⁃
der Mild Condition〔J〕. Res Chem Intermediat，2016，42：
6089-6103.
〔20〕 WANG L H，LEI T，WANG F S，et al. Total Synthesis of
Indiacen A Using a Practical One-Pot Reaction：Promoted
by a Key Waste Product，and Its Utility in Natural Products
Synthesis〔J〕. Tetrahedron Lett，2021，66：152822.
〔21〕 LI T，SONG J J，WANG L H，et al. A Simple and Efficient
Total Synthesis of Anticancer Indole Alkaloids TMC-205
and Its Analogues〔J〕. Tetrahedron Lett，2021，74：153137.
〔22〕 SONG J J，LU G D，YANG B Q，et al. A Concise First To⁃
tal Synthesis of Luteoride A and Luteoride B〔J〕. Tetrahe⁃
dron，2022，122：132933.
