112031-10-4Relevant articles and documents
A Novel Synthesis of (R)- and (S)-4-Hydroxytetrahydrofuran-2-ones
Tanaka, Akira,Yamashita, Kyohei
, p. 570 - 573 (1987)
A practical synthesis of (R)- and (S)-4-hydroxytetrahydrofuran-2-ones is accomplished starting from L-ascorbic acid and D-isoascorbic acid, respectively.
Stereoselective synthesis of tetrahydropyranyl diarylheptanoids (-)-centrolobine and (+)-centrolobine
Reddy, Chada Raji,Madhavi, Pasupulety Phani,Chandrasekhar, Srivari
experimental part, p. 123 - 126 (2011/02/26)
A versatile chiron approach to the tetrahydropyranyl diarylheptanoid natural products (-)-centrolobine and (+)-centrolobine has been described. The use of an aldol reaction followed by reductive etherification for the formation of tetrahydropyran ring is of importance. Georg Thieme Verlag Stuttgart · New York.
Synthesis of medium ring ethers. 5. The synthesis of (±)-laurencin
Burton, Jonathan W.,Clark, J. Stephen,Derrer, Sam,Stork, Thomas C.,Bendall, Justin G.,Holmes, Andrew B.
, p. 7483 - 7498 (2007/10/03)
The enantioselective synthesis of (+)-laurencin 1 has been achieved in 27 steps from (R)-malic acid 20. The key steps involved methylenation of the lactone 49 followed by intramolecular hydrosilation of the enol ether 14 (Scheme 11) and one carbon homologation of the diol 13 to give the key ethyl substituted cyclic ether 59 (Scheme 13). The lactone 49 was obtained by two efficient routes, namely a Claisen ring expansion (Scheme 3) followed by cl-hydroxylation (Scheme 6) and a Yamaguchi lactonization (Scheme 11). Elaboration of the (E)-pentenynyl side chain (Scheme 18) and introduction of bromine (Scheme 19) completed the synthesis of (+)-laurencin 1.
