Total synthesis of (+)-phomopsolide C by ring-size selective ring-closing metathesis/cross-metathesis.
[reaction: see text]A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.
Michaelis
Simon
S
Institut für Chemie, Technische Universität Berlin, Strasse des 17.Juni 135, 10623 Berlin, Germany.
Blechert
Siegfried
S
D003500:Cyclization; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011753:Pyrones; C512390:phomopsolide C