Total synthesis of (−)-jaspine B and its 4-epi-analogue from d-xylose

Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation

“…in 2002. 16 Herein, we now propose a practical approach to its synthesis starting from the allylic alcohol 2. 14 They also reported the isolation and characterization of jaspine A and the structurally related jaspine B analogues including 2-epi jaspine B from the same species (Fig.…”

“…Although several reports are available in the literature for the synthesis of jaspine B, only a few synthetic approaches have been disclosed for the synthesis of 2epi jaspine B since its isolation. 16 Herein, we now propose a practical approach to its synthesis starting from the allylic alcohol 2. As per our retro synthetic analysis delineated in Scheme 7, the stereostructure of the major isomer 4a obtained via iodocycloetherification of 2 as discussed above had stereostructural resemblance to 2-epi jaspine B and therefore, it could be utilized as a key intermediate to complete the total synthesis of the title natural product.…”

Synthesis and Biological Evaluation of Carbocyclic Analogues of Pachastrissamine

“…It was also reported that pachastrissamine and its stereoisomers inhibit sphingosine kinases (SphKs) and atypical protein kinase C [ 5 ]. Because of its intriguing biological activity, it has been an interesting target for synthetic chemists, and various synthetic routes to pachastrissamine have been reported [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. However, the structure-activity relationship (SAR) of pachastrissamine remains relatively unreported.…”

Practical Synthesis of Pachastrissamine (Jaspine B), 2-<i>epi</i>-Pachastrissamine, and the 2-<i>epi</i>-Pyrrolidine Analogue

“…9,10) Because of its novel structural features and impressive biological activity, many total syntheses of 1 have been accomplished. [3][4][5][6][7][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] The stereoisomers of 1 have also been synthesized, 5,6,[20][21][22][23][24][25][26][27][28][29][31][32][33][34][35][36][37][38][39][40] and their biological activity investigated. Interestingly, the 2-epimer 2 6,…”