Petromyroxol (3) was isolated from > 106 liters of sea water conditioned with
larval sea lamprey, Petromyzon marinus. Rodney A. Fernandes of the Indian
Institute of Technology Bombay assembled the core of 3 by selectively cyclizing
the diol 1 to the
tetrahydrofuran 2
(Chem. Commun. 5-Amino-6-methylnicotinonitrile In stock 2023, 59, 2007,
DOI: 10.1039/D2CC04579F;
Chem. 1346270-08-3 Chemscene Commun. 2022, 58, 11921,
DOI: 10.1039/D2CC04574E).
Hedyosumin A (7) was isolated from the aerial parts of the Chinese flowering
plant Hedyosmum orientale. Jia-Hua Chen and Zhen Yang of Peking University
constructed the tricyclic core 6 of 7 by the Pt-catalyzed coupling of the keto
alkyne 4 with acetaldehyde silyl enol ether 5
(Tetrahedron Lett. 2022, 102, 153946.
DOI: 10.1016/j.tetlet.2022.153946). PMID:36628218
Cephalosporolide J (10) was isolated during a bioassay-guided investigation of
the deep-sea derived fungus Penicillium commune. Koichiro Ota and Hiroaki
Miyaoka of the Tokyo University of Pharmacy and Life Sciences initiated their
synthesis of 10 with the
Sharpless asymmetric dihydroxylation of the unsaturated
ester 8, leading to the lactone 9
(Synlett 2022, 34, 271).
Fernando Sartillo-Piscil reported a parallel investigation
(J. Org. Chem. 2023, 88, 4880.
DOI: 10.1021/acs.joc.3c00251).
Malettenin C (13) was isolated from the stromata of Hypoxylon sp. growing on
dead aspen logs. Following the lead of Kende and Koch, Satoshi Yokoshima of
Nagoya University assembled the tropolone 12 by the oxidative cyclization of the
phenol 11, followed by treatment with base
(Org. Lett. 2023, 25, 4530.
DOI: 10.1021/acs.orglett.3c01565).
Originally isolated from the marine fungus Xylaria sp. of the South China Sea,
xyloketal B (17) protects endothelial cells from oxidized LDL-induced injury at
0.3 µM. Alison R. H. Narayan of the University of Michigan assembled the
precursor iodide 16 by the diastereoselective combination of the triol 14 with
the dihydrofuran 15
(Org. Lett. 2023, 25, 1547.
DOI: 10.1021/acs.orglett.3c00334).
Lucidumone (20), isolated from the mushroom Ganoderma lucidum, selectively
inhibits COX-2. En route to 20, Yuichiro Kawamoto and Hisanaka Ito, also of the
Tokyo University of Pharmacy and Life Sciences, selectively cyclized the triol
18 to the pentacyclic ether 19
(Angew. Chem. Int. Ed. 2023, 62, e202304132.
DOI: 10.1002/anie.202304132).
