Total synthesis of (+)-achalensolide based on the rh(i)-catalyzed allenic Pauson-Khand-type reaction.
The first total synthesis of (+)-achalensolide was achieved from a commercially available d-(-)-isoascorbic acid. The known epoxide, derived from d-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.
Hirose
Toshiyuki
T
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Miyakoshi
Naoki
N
Mukai
Chisato
C
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
D000466:Alkadienes; D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; C527592:achalensolide; C025947:propadiene; D012238:Rhodium