General preparation and controlled cyclization of acyclic terpenoids.
A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C5 unit 5 and the chain-termination process utilizing the C5 unit 10 together with the chemoselective reductive desulfonylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon-carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups.
Kuk
Jinchul
J
Department of Nano Science and Engineering, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea.
Kim
Beom Soo
BS
Jung
Heejung
H
Choi
Seyoung
S
Park
Jung-Youl
JY
Koo
Sangho
S
D003500:Cyclization; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000737:chemistry*
D013729:Terpenes