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2004
Rings with 7 or more members
Q 0050
Stereoselective Synthesis of Bicyclo[4.2.1]nonane Skeletons by Ring-Closing MetA New Versatile Methodology for the Efficient Assembly of Functional50- 048 athesis:
ized Cyclooctanoids. — The title methology combines a stereoselective anionic domino α,γ-difunctionalization of β-ketoesters with ring-closing metathesis resulting in a
formal three-carbon ring expansion. Direct retro-Dieckmann cleavage of bridged
ketone (IIa) to liberate the corresponding fused eight-membered is carried out producing a 1:1 mixture of the diastereomers. Product (XI) is successfully transformed to the
corresponding monotosylate precursor for a stereoselective Grob-type fragmentation.
On reaction with KHMDS in THF, aldehyde (XII) is produced diastereoselectively in
45% yield. — (MICHAUT, A.; MIRANDA-GARCIA, S.; MENENDEZ, J. C.;
RODRIGUEZ*, J.; Org. Lett. 6 (2004) 18, 3075-3078; React. Synth. Org., Cent. St.
Jerome, Univ. Paul Cezanne, F-13397 Marseille, Fr.; Eng.) — Steudel
2004
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