872035-33-1Relevant academic research and scientific papers
Total syntheses of naturally occurring seimatopolide A and its enantiomer from chiral pool starting materials using a bidirectional strategy
Schmidt, Bernd,Kunz, Oliver,Petersen, Monib H.
, p. 10897 - 10906 (2013/02/22)
Enantioselective total syntheses of both enantiomers of the recently isolated decanolide natural product seimatopolide A are described. The C 2-symmetric building blocks (R,R)-hexa-1,5-diene-3,4-diol (derived from d-mannitol) and its enantiomer (derived from l-(+)-tartrate) serve as key starting materials, which are elaborated in a bidirectional way using a selective mono-cross-metathesis, regio-and stereoselective epoxidation, and regioselective reductive epoxide opening to furnish the first fragment. Both enantiomers of the second fragment, 3-hydroxypent-4-enoic acid, were conveniently obtained through a lipase-catalyzed kinetic resolution and merged with the first fragment via Shiina esterification. An E-selective ring-closing metathesis was used to access the 10-membered lactone. A comparison of the specific optical rotations of synthetic seimatopolides with those reported for the natural product suggests that the originally assigned (3R,6R,7R,9S)- configuration should be corrected to (3S,6S,7S,9R).
Total synthesis of (+)-phomopsolide C by ring-size selective ring-closing metathesis/cross-metathesis
Michaelis, Simon,Blechert, Siegfried
, p. 5513 - 5516 (2007/10/03)
(Chemical Equation Presented) 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 describe
