Total synthesis of (+)-crocacin D.
[structure: see text] The first asymmetric synthesis of (+)-crocacin D (4) is described. The key steps in the sequence are the stereoselective assembly of the stereotetrad via a substrate-controlled aldol reaction and anti-selective reduction, formation of the (E,E)-diene by a Stille cross-coupling between the stannane 8 and vinyl iodide 9, and the acylation of (Z)-enecarbamate 6 with the acid chloride derived from polyketide fragment 16 which introduced the (Z)-enamide functionality.
Feutrill
John T
JT
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Lilly
Michael J
MJ
Rizzacasa
Mark A
MA
D000577:Amides / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D004579:Electron Transport / Q000187:drug effects; D005658:Fungi / Q000737:chemistry*; D007202:Indicators and Reagents; D008968:Molecular Conformation
D000577:Amides; D000935:Antifungal Agents; D007202:Indicators and Reagents; C451481:crocacin D