
Tetrahedron p. 4243 - 4250 (1998)
Update date:2022-08-12
Topics:
Okuma, Kentaro
Hirabayashi, Syun-ichi
Ono, Masaaki
Shioji, Kosei
Matsuyama, Haruo
Bestmann, Hans J.
E-(R)-(+)-8-Dodece- 11-olide, which is known as recifeiolide, was synthesized by a six-step reaction starting from (R)-(+)-propene oxide in a total yield of 53 %. The key step of this synthesis is the preparation of (R)-(-)-methyl 11-hydroxy-8-dodecenate using (R)-(-)-5-methyl-2,2,2- triphenyl-1,2λ5-oxaphospholane. By using this method, enantiomerically pure 13- and 14-membered macrolides were also synthesized.
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