Asymmetric synthesis of the fully functionalized cyclodecene core of naturally occurring sesquiterpene hypocoprins A-C

被引：0

作者：

Soni, Chandan Kumar ^{[1
]}

Mandal, Kishor Kumar ^{[1
]}

Sarkar, Rajarshee ^{[1
]}

Nanda, Samik ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, India

来源：

TETRAHEDRON | 2024年 / 163卷

关键词：

Cyclopropane containing sesquiterpenoid; Total synthesis; Ring closing metathesis; Asymmetric cyclopropanation; Synthetic strategy; TRANSFER HYDROGENATION; EMMONS MODIFICATION; SECONDARY ALCOHOLS; ALLYLIC ALCOHOLS; AROMATIC KETONES; WITTIG REACTION; HYDROZIRCONATION; CYCLOPROPANATION; TRIETHYLAMINE; ALDEHYDES;

D O I：

10.1016/j.tet.2024.134143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of fully functionalized E-cyclodecene core of naturally occurring cyclopropane containing sesquiterpenoid hypocoprins A-C was accomplished. Intramolecular HWE olefination and NHK-coupling reaction failed to provide the desired E-cyclodecene core. Finally, late stage ring closing metathesis (RCM) reaction enables the construction of fully functionalized E-cyclodecene-core of the natural products. Substrate-directed cyclopropanation and Noyori's asymmetric transfer hydrogenation are the key reactions employed to access the RCM precursor.

引用

页数：16

共 42 条

[1] Z-Selective Intramolecular Horner-Wadsworth-Emmons Reaction for the Synthesis of Macrocyclic Lactones
Ando, Kaori
Narumiya, Kenji
Takada, Hirokazu
Teruya, Taiji
[J]. ORGANIC LETTERS, 2010, 12 (07) : 1460 - 1463
[2] Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one
Barik, Rasmita
Nanda, Samik
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (22) : 4478 - 4487
[3] Coprophilous fungi: antibiotic discovery and functions in an underexplored arena of microbial defensive mutualism
Bills, Gerald F.
Gloer, James B.
An, Zhiqiang
[J]. CURRENT OPINION IN MICROBIOLOGY, 2013, 16 (05) : 549 - 565
[4] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[5] Asymmetric synthesis of (2-carbamoyloxy-1-alkenyl)cyclopropanes by intramolecular cycloalkylation
Brandau, S
Hoppe, D
[J]. TETRAHEDRON, 2005, 61 (52) : 12244 - 12255
[6] Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction
Charette, AB
Molinaro, C
Brochu, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12168 - 12175
[7] Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications
Charette, AB
Juteau, H
Lebel, H
Molinaro, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) : 11943 - 11952
[8] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
COREY, EJ
BAKSHI, RK
SHIBATA, S
CHEN, CP
SINGH, VK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7925 - 7926
[9] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[10] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156

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