152203-66-2Relevant academic research and scientific papers
Total synthesis of (R)-(+)-kavain via (MeCN)2PdCl 2-catalyzed isomerization of a cis double bond and sonochemical Blaise reaction
Wang, Fang-Dao,Yue, Jian-Min
, p. 2077 - 2079 (2005)
From the chiral source 2,3-O-isopropylidene-D-glyceraldehyde 2, the natural product (R)-(+)-kavain 1a was efficiently synthesized in a total yield of 25% via (MeCN)2PdCl2-catalyzed isomerization of the cis double bond of an olefin as the key step and sonochemical Biaise reaction. The chiral center adjacent to the cis double bond was retained without protection of the free allylic hydroxy during the isomerization process. Georg Thieme Verlag Stuttgart.
Total Synthesis of Meayamycin B
Basu, Upamanyu,Bressin, Robert K.,Koide, Kazunori,Osman, Sami,Pohorilets, Ivanna
supporting information, p. 4637 - 4647 (2020/05/01)
Meayamycin B is currently the most potent modulator of the splicing factor 3b subunit 1 and used by dozens of research groups. However, current supply for this natural product analogue is limited because of the lengthy synthetic scheme. Here, we report a more concise, more cost-effective, and greener synthesis of this compound by developing and employing a novel asymmetric reduction of a prochiral enone to afford an allylic alcohol with high enantioselectivity. In addition to this reaction, this synthesis highlights a scalable Mukaiyama aldol reaction, Nicolaou-type epoxide opening reaction, stereoselective Corey-Chaykovsky-type reaction, and a modified Horner-Wadsworth-Emmons Z-selective olefination. We also discuss a Z-E isomerization during the α,β-unsaturated amide formation. The new synthesis of meayamycin B consists of 11 steps in the longest linear sequence and 24 total steps.
Rearrangement of Allylic Cyclic Sulfites to Allylic Sultones
Duffy, Daniel E.,Condit, Fletcher H.,Teleha, Christopher,Wang, Chia-Lin J.,Calabrese, Joseph C.
, p. 3667 - 3670 (2007/10/02)
Rearrangement of allylic cyclic sulfites 2 to allylic sultones 8 upon treatment with boron trifluoride etherate is described.
