Reduction: The Tadpetch Synthesis of Pestalotioprolide B
Chemexpress Xiongjie Jin and Kyoko Nozaki of the University of Tokyo established an effective protocol for the hydrogenation of an ester 1 to the corresponding hydrocarbon 2 (J. Am. Chem. Soc.…
C-O Ring Construction: Petromyroxol (Fernandes), Hedyosumin A (Chen/Yang), Cephalosporolide J (Ota/Miyaoka), Malettenin C (Yokoshima), xyloketal B (Narayan), Lucidumone (Kawamoto/Ito)
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…
Alkylated Stereogenic Centers: The Tambar Synthesis of Enterolactone
Qiwei Lang, Gen-Qiang Chen and Xumu Zhang of the Southern University of Science and Technology achieved high ee in the reduction of the readily available lactol 1 to the lactone…
Rare Sugars Are Now Readily Available Chiral Pool Starting Materials
Many of the five- and six-carbon sugars, although well known, are rare, and too expensive to be used as chiral pool starting materials. David MacMillan of Caltech in an elegant…
Functional Group Interconversion: The Nagasawa/Iwabuchi Synthesis of Rumphellclovane E
Christopher B. 2-Aminoacetamide uses Kelly of Janssen Discovery Process, Osvaldo Gutierrez of Texas A&M and Mark D. Levin of the University of Chicago used the N-acyloxy N-alkoxy amide 2 to…
Enantioselective Synthesis of Alcohols and Amines: The Lin/Liu Route to Haliclamide
Benjamin List of the Max-Planck-Institut für Kohlenforschung used a confined imidodiphosphorimidate to catalyze the cyclization of the unsaturated acid 1 to the lactone 2 (J. Am. Chem. Soc. 2023, 145,…
The Suzuki/Tanino Synthesis of Kamebanin
Kamebanin (3), isolated from the Japanese flowering plant Isodon kameba Okuyama (Isodon umbrosus), showed cytotoxic and antibiotic activity. Takahiro Suzuki and Keiji Tanino of Hokkaido University devised a route to…
C-O Ring Construction: The Menche Synthesis of Pentamycin
Guisheng Zhang and Zhiguo Zhang of Henan Normal University rearranged the activated cyclopropane 1 with catalytic 2, leading to the dihydrofuran 3 (J. Org. PMID:23800738 Chem. 2023, 88, 1003. DOI:…
The Baran Synthesis of Cyclopamine
Cyclopamine (4), a teratogenic alkaloid isolated from the California corn lily Veratrum californicum, has been shown to disrupt the hedgehog signalling pathway. Phil S. Baran of Scripps/La Jolla envisioned a…
The Fan Synthesis of Trachinol
Trachinol (3), isolated fifty years ago from Sideritis canariensis Ait., a shrub of the Canary Islands, has an intriguing pentacyclic structure. Chun-An Fan of Lanzhou University devised an elegant preparation…