First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B

被引：2

作者：

Canko, Aleksander ^{[1
,2
]}

Athanassopoulou, Georgia D. D. ^{[1
]}

Psycharis, Vassilis ^{[1
]}

Raptopoulou, Catherine P. P. ^{[1
]}

Herniman, Julie M. M. ^{[3
]}

Mouchtouris, Vasileios ^{[4
,5
]}

Foscolos, Angeliki Sofia ^{[1
]}

Couladouros, Elias A. A. ^{[2
]}

Vidali, Veroniki P. P. ^{[1
]}

机构：

[1] NCSR Demokritos, Inst Nanosci & Nanotechnol, Athens, Greece

[2] Agr Univ Athens, Dept Food Sci & Human Nutr, Athens, Greece

[3] Univ Southampton, Fac Engn & Phys Sci, Sch Chem, Southampton, England

[4] Univ Copenhagen, Nanosci Ctr, Copenhagen, Denmark

[5] Univ Copenhagen, Dept Chem, Copenhagen, Denmark

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 18期

关键词：

DIELS-ALDER REACTIONS; MARINE VERRUCOSISPORA STRAIN; BIOLOGICAL EVALUATION; FLUORINATED ALCOHOLS; MICHAEL ADDITION; ACID; HEXAFLUOROISOPROPANOL; CONSTRUCTION; POLYKETIDE; INHIBITOR;

D O I：

10.1039/d3ob00476g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Diels-Alder reaction (IMDA) of a butenolide derivative, as an entry to the type II abyssomicin scaffold, and the total synthesis of (+/-)-abyssomicin 2 and (+/-)-neoabyssomicin B are reported for the first time. A facile route to the IMDA precursor, the formation of a type I intermediate and two paths to (+/-)-neoabyssomicin B are also discussed.

引用

页码：3761 / 3765

页数：5

共 50 条

[31] Total Synthesis of Floyocidin B: 4,5-Regioselective Functionalization of 2-Chloropyridines
Kleiner, Yolanda
Bauer, Armin
Hammann, Peter
Schuler, Soeren M. M.
Poeverlein, Christoph
CHEMISTRY-SWITZERLAND, 2023, 5 (01): : 168 - 178
[32] Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II
Adler, Marc J.
Baldwin, Steven W.
TETRAHEDRON LETTERS, 2009, 50 (36) : 5075 - 5079
[33] Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E
Kutz, Sebastian K.
Boerger, Carsten
Schmidt, Arndt W.
Knoelker, Hans-Joachim
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (07) : 2487 - 2500
[34] Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol
Nguyen, Minh H.
Imanishi, Masashi
Kurogi, Taichi
Smith, Amos B., III
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (11) : 3675 - 3678
[35] CuBr2-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers
Padhi, Birakishore
Reddy, G. Sudhakar
Mallampudi, N. Arjunreddy
Choudhury, Utkat Mani
Mohapatra, Debendra K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (14) : 2685 - 2695
[36] Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland-Japp derived 2H-dihydropyran-4-ones: a total synthesis of diospongin B
Clarke, Paul A.
Nasir, Nadiah Mad
Sellars, Philip B.
Peter, Alejandra M.
Lawson, Connor A.
Burroughs, James L.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (28) : 6840 - 6852
[37] Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (-)-9,10-Dihydroecklonialactone B
Becker, Julia
Butt, Lena
von Kiedrowski, Valeska
Mischler, Elisabeth
Quentin, Florian
Hiersemann, Martin
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) : 3040 - 3051
[38] Rh-Catalyzed [2+2+2] Cycloadditions with Benzoquinones: De Novo Access to Naphthoquinones for Lignan and Type II Polyketide Synthesis
Wood, James M.
da Silva Junior, Eufranio N.
Bower, John F.
ORGANIC LETTERS, 2020, 22 (01) : 265 - 269
[39] Synthesis and characterization of hyperbranched polyimides from a novel B′B2-type triamine with tert-butyl side group
Yi, Lang
Wu, Xiuming
Shu, Chen
Huang, Wei
Yan, Deyue
POLYMER, 2017, 133 : 171 - 183
[40] Synthesis, characterization, thermal and antimicrobial studies of diabetic drug models: Complexes of vanadyl(II) sulfate with ascorbic acid (vitamin C), riboflavin (vitamin B2) and nicotinamide (vitamin B3)
Refat, Moamen S.
JOURNAL OF MOLECULAR STRUCTURE, 2010, 969 (1-3) : 163 - 171

← 1 2 3 4 5 →