Concise total syntheses of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one.
Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Shibing
S
Tang
Xingang
X
Xie
Xiaolei
X
Wang
Liuer
L
He
Ke
K
Xu
Xuegong
X
She
D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
C555844:(6R)-6-((4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl)-5,6-dihydro-2H-pyran-2-one; D000447:Aldehydes; D001880:Boranes; D011753:Pyrones; C476921:strictifolione; C085538:3-butenal