Network


Latest external collaboration on country level. Dive into details by clicking on the dots.

Hotspot


Dive into the research topics where Dae-Shik Kim is active.

Publication


Featured researches published by Dae-Shik Kim.


Journal of the American Chemical Society | 2009

New Syntheses of E7389 C14−C35 and Halichondrin C14−C38 Building Blocks: Double-Inversion Approach

Dae-Shik Kim; Cheng-Guo Dong; Joseph T. Kim; Haibing Guo; Jian Huang; Paolo S. Tiseni; Yoshito Kishi

With sequential use of catalytic asymmetric Cr-mediated coupling reactions, E7389 C14-C35 and halichondrin C14-C38 building blocks have been stereoselectively synthesized. The C19-C20 bond is first formed via the catalytic asymmetric Ni/Cr-mediated coupling, i.e., 8 + 9 --> 10 (90%; dr = 22:1), in which vinyl iodide 8 is used as the limiting substrate. The C23-C24 bond is then formed via the catalytic asymmetric Co/Cr-mediated coupling, i.e., 13 + 14 --> 4 (82%; dr = 22:1), in which the alkyl-iodide bond in 14 is selectively activated over the vinyl-iodide bond. The catalytic asymmetric Ni/Cr-mediated reaction is employed to couple C14-C26 segment 19 with E7389 C27-C35 segment 20 (91%; dr = >55:1). In this synthesis, the C23-O bond is stereoselectively constructed via a double-inversion process, i.e., 21 --> 22, to furnish E7389 C14-C35 building block 22 in 84% yield. The same synthetic sequence has been employed to synthesize halichondrin C14-C38 building block 18b, i.e., 16a + 19 --> 18b.


Organic Letters | 2009

Second Generation Synthesis of C27−C35 Building Block of E7389, a Synthetic Halichondrin Analogue

Yu-Rong Yang; Dae-Shik Kim; Yoshito Kishi

A practical method is reported to synthesize E7389 C27-C35 building block 13 from 1,2-O-isopropylidene-alpha-D-5-deoxyglucurono-6,3-lactone (3). This synthesis relies on two key processes: (1) C34/C35-diol is introduced via asymmetric dihydroxylation with dr = 3:1, with the undesired C34-diastereomer effectively removed by crystallization of 11, and (2) the C30 PhSO2CH2 group is introduced stereoselectively (>100:1) via hydrogenation of 12 in the presence of the Crabtree catalyst. The reported synthesis is practically free from chromatographic separation.


Organic Letters | 2017

Prins Reaction of Homoallenyl Alcohols: Access to Substituted Pyrans in the Halichondrin Series

Hyeong-wook Choi; Francis G. Fang; Hui Fang; Dae-Shik Kim; Steven Mathieu; Robert T. Yu

Prins reaction of homoallenyl alcohols with aldehyde dimethylacetals in the presence of methoxyacetic acid directly affords tetrasubstituted pyrans relevant to halichondrins with complete control of the C27 stereogenic center. Regioselective Tsuji reduction of the resultant allylic acetates stereoselectively establishes the C25 stereogenic center and C26 exocyclic olefin. Building upon these findings, we achieved concise access to the halichondrin C14-C38 and eribulin C14-C35 fragments.


Journal of Organic Chemistry | 2006

A general, convergent strategy for the construction of indolizidine alkaloids : Total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B

Amos B. Smith; Dae-Shik Kim


Journal of the American Chemical Society | 2009

Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions

Haibing Guo; Cheng-Guo Dong; Dae-Shik Kim; Daisuke Urabe; Jiashi Wang; Joseph T. Kim; Xiang Liu; Takeo Sasaki; Yoshito Kishi


Organic Letters | 2005

Total synthesis of the neotropical poison-frog alkaloid (-)-205B.

Iii and Amos B. Smith; Dae-Shik Kim


Organic Letters | 2004

Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: synthesis of (-)-indolizidine 223AB.

Iii and Amos B. Smith; Dae-Shik Kim


Organic Letters | 2007

The Spirastrellolides: Construction of the Southern C(1)−C(25) Fragment Exploiting Anion Relay Chemistry

Iii and Amos B. Smith; Dae-Shik Kim


Journal of the American Chemical Society | 2006

The [1,5]-brook rearrangement : An initial application in anion relay chemistry

Amos B. Smith; Ming Xian; Wonsuk Kim; Dae-Shik Kim


Archive | 2016

Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides

Francis G. Fang; Charles E. Chase; Dae-Shik Kim; Hyeong-wook Choi

Collaboration


Dive into the Dae-Shik Kim's collaboration.

Top Co-Authors

Avatar
Top Co-Authors

Avatar
Top Co-Authors

Avatar

Amos B. Smith

University of Pennsylvania

View shared research outputs
Top Co-Authors

Avatar

Joseph T. Kim

University of Illinois at Chicago

View shared research outputs
Top Co-Authors

Avatar
Top Co-Authors

Avatar
Researchain Logo
Decentralizing Knowledge