Tetrahedron p. 11471 - 11480 (1998)
Update date:2022-07-30
Topics:
Berkenbusch, Thilo
Brueckner, Reinhard
An enantioselective synthesis of (+)-ginnol (17) illustrates how Sharpless' asymmetric dihydroxylation may be used for the asymmetric synthesis of monoalcohols. The dihydroxylation was perfomed with AD mix α and the unsaturated ester trans-9. The resulting lactone cis-13 was dehydrated giving butenolide 13 (96.2% ee) from where we proceeded to the title compound 17 in three steps. Butenolide 13 showed 88-94%ee when ester trans-9 contained cis-isomer due to too forcing reaction condition on the way to the precursor acids trans- and cis-7.
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