Short and efficient route to the fully functionalized polar core of scyphostatin.
[reaction: see text]. Diastereoselective oxidative dearomatization of benzopyran 5 to the corresponding p-quinol 9b allows a fast, efficient, and versatile entry to scyphostatin's polar epoxycyclohexenone moiety as demonstrated by the preparation of its palmitoyl analogue 16 (R = (CH2)14CH3).
Pitsinos
Emmanuel N
EN
Laboratory of Natural Products Synthesis and Bioorganic Chemistry, Institute of Physical Chemistry, NCSR Demokritos, P.O. Box 60228, GR-153 10 Aghia Paraskevi, Athens, Greece. pitsinos@chem.demokritos.gr
Cruz
Ana
A
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010168:Palmitates / Q000138:chemical synthesis; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
D000577:Amides; D004791:Enzyme Inhibitors; D010168:Palmitates; D011753:Pyrones; C121123:scyphostatin; D013108:Sphingomyelin Phosphodiesterase