72229-13-1Relevant articles and documents
Stereoselective synthesis of tetrahydropyrans through tandem and organocatalytic oxa-Michael reactions: Synthesis of the tetrahydropyran cores of ent-(+)-sorangicin A
Lee, Kiyoun,Kim, Hyoungsu,Hong, Jiyong
, p. 1025 - 1032 (2012/03/27)
Tandem and organocatalytic oxa-Michael reactions of α,β- unsaturated aldehydes were explored for the stereoselective synthesis of structurally complex tetrahydropyrans. Thestereoselective synthesis of 2,6-trans-tetrahydropyrans, which are thermodynamically unfavorable, was accomplished through a reagent-controlled, organocatalytic oxa-Michael reaction. A temperature-dependent configurational switch allowed the preparation of both 2,3-trans-2,6-trans-and 2,3-cis-2,6-cis-tetrahydropyrans from a common substrate. This switch was then used to synthesize the precursors of the C21-C29 and C30-C37 fragments of ent-(+)-sorangicin A. The tandem and organocatalytic oxa-Michael reactions of α,β-unsaturated aldehydes were explored and applied to the stereoselective synthesis of structurally complex tetrahydropyrans. Copyright
Formal synthesis of (+)-isolaurepinnacin
Suzuki, Toshio,Matsumura, Ryuji,Oku, Ken-ichi,Taguchi, Keiichi,Hagiwara, Hisahiro,Hoshi, Takashi,Ando, Masayoshi
, p. 65 - 67 (2007/10/03)
The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the α,ω-positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)2O/Zn(OTf)2 system.
Formal Synthesis of a Unsaturated Trihydroxy C-18 Fatty Acid
Sharma, Pradeep Kumar
, p. 1825 - 1826 (2007/10/02)
Stereoselective synthesis of (4R,5S)-2,2-dimethyl-5--1,3-dioxolane-4-carboxaldehyde, a key intermediate for the synthesis of (9S, 12S, 13S)-trihydroxy-(10E, 15Z)-octadecadienoic acid starting from cis-butene-1,4-diol, is described.
