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(S)-(-)-5-Hydroxymethyl-2(5H)-furanone is used in the preparation of partially saturated heterocycles via a diastereoselective ring chain formation. It is also used in the synthesis of (1R,3S)-cis-chrysanthemic acid.
Kyung Ho Kang.; Mi Young Cha.; Ae Nim Pae.; Kyung Il Choi.; Yong Seo Cho.; Hun Yeong Koh,; Bong Young Chung. Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2(5H)-furanone. Tetrahedron Letters. 2000, 41 (42), 8137-8140.
Vladimír Ondruša.; Michal Orsága.; L'ubor Fišeraa.; Nad'a Prónayován. Stereoselectivity of N-benzyl-C-ethoxycarbonyl nitrone cycloaddition to (S)-5-hydroxymethyl-2(5H)-furanone and its derivatives. Tetrahedron. 1999, 55 (34), 10425-10436.
Versatile chiral intermediate.
For use in the synthesis of (1R,3S)-cis-chrysanthemic acid, see: Tetrahedron Lett., 27, 3533 (1986).
In enantioselective synthesis of AZT: Tetrahedron Lett., 29, 5349 (1988).