82206-87-9Relevant academic research and scientific papers
Total syntheses of ainsliadimer B and gochnatiolides A and B
Xia, Dongliang,Du, Yu,Yi, Zhi,Song, Hao,Qin, Yong
, p. 4423 - 4427 (2013/05/09)
Oh my goch: The total syntheses of ainsliadimer B and gochnatiolides A and B from α-santonin have been accomplished in 25 steps with approximately 1 % overall yield. A Diels-Alder reaction of natural dehydrozaluzanin C with a monomeric guaianolide derivative allows stereoselective assembly of a dimeric gochnatiolide-type skeleton with the required stereochemistry and preinstalled functionalities for the synthesis of dimeric ainsliadimer B and gochnatiolides A and B (see scheme). Copyright
Studies on the Syntheses of Sesquiterpene Lactones. 11. The Syntheses of 3-Epizaluzanin C, Zaluzanin C, Zaluzanin D, and Related Compounds 3&α-Hydroxyguaia-1(10),4(15),11(13)-trieno-12,6&α-lactone and 3&α-Hydroxyguaia-4(15),9,11(13)-trieno-12,6&α-lactone
Ando, Masayoshi,Kusaka, Haruhiko,Ohara, Hiroshi,Takase, Kahei,Yamaoka, Hiroaki,Yanagi, Yoshikazu
, p. 1952 - 1960 (2007/10/02)
3-Epizaluzanin C (10), 3α-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6α-lactone (36), and 3α-hydroxyguaia-4(15),9,11(13)-trieno-12,6α-lactone (37) have been synthesized in 4.0percent, 3.0percent, and 1.7percent overall yields, respectively, from α-santonine (13) in 14 steps.Zaluzanin C (11) and zaluzanin D (12) have also been synthesized in 2.4percent and 2.5percent overall yields from α-santonin (13) in 16 steps and 15 steps, respectively.The key step involves the solvolytic rearrangement of (11S)-3α,4α-epoxy-1β-(mesyloxy)eudesmano-13,6α-lactone (27).The stereochemistry of3-epizaluzanin C (10), zaluzanin C (11), and zaluzanin D (12) have been established by these stereospecific syntheses.
TOTAL SYNTHESIS OF ZALUZANIN C, ZALUZANIN D, AND 3-EPIZALUZANIN C
Ando, Masayoshi,Yamaoka, Hiroaki,Takase, Kahei
, p. 501 - 504 (2007/10/02)
The biologically active guaianolides, zaluzanin C, and zaluzanin D, and the stereoisomeric guaianolide, 3-epizaluzanin C have been synthesized by two different procedures.The stereochemistry at C3 of zaluzanin C has been established to be S configuration by this synthesis.
