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

DOI: 10.1016/S0040-4020(98)00142-2

Source and publish data:

Tetrahedron p. 4243 - 4250 (1998)

Update date:2022-08-12

Topics:

Authors:

Okuma, Kentaro

Hirabayashi, Syun-ichi

Ono, Masaaki

Shioji, Kosei

Matsuyama, Haruo

Bestmann, Hans J.

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Article abstract of DOI:10.1016/S0040-4020(98)00142-2

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.

Full text of DOI:10.1016/S0040-4020(98)00142-2

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