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An efficient synthesis of (R)-(+)-recifeiolide and related macrolides by using enantiomerically pure (R)-(−)-5-methyl-2,2,2-triphenyl-1,2λ5-oxaphospholane

✍ Scribed by Kentaro Okuma; Syun-ichi Hirabayashi; Masaaki Ono; Kosei Shioji; Haruo Matsuyama; Hans J Bestmann

Book ID
104208496
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
537 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

E-(R)-(+)-8-Dodece-ll-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-t,2X 5oxaphospholane. By using this method, enantiomerically pure 13-and 14-membered macrolides were also synthesized.

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