Concise Total Synthesis of (+)-Luteoalbusins A and B
The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel–Crafts C3-indole addition to a cyclotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulf...
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| Published in | Organic letters Vol. 17; no. 17; pp. 4268 - 4271 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
04.09.2015
Amer Chemical Soc |
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| Abstract | The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel–Crafts C3-indole addition to a cyclotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, HeLa, HCT116, and MCF7 human cancer cell lines. |
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| AbstractList | The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cyclotryptophan derived diketopiperazine, a late-stage diketopiperazine dihydroxylation and C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, HeLa, HCT116 and MCF7 human cancer cell lines. The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cyclotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, HeLa, HCT116, and MCF7 human cancer cell lines. The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cydotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, He La, HCT116, and MCF7 human cancer cell lines. |
| Author | Movassaghi, Mohammad Adams, Timothy C Payette, Joshua N Cheah, Jaime H |
| AuthorAffiliation | Department of Chemistry The Koch Institute for Integrative Cancer Research Massachusetts Institute of Technology |
| AuthorAffiliation_xml | – name: The Koch Institute for Integrative Cancer Research – name: Massachusetts Institute of Technology – name: Department of Chemistry – name: The Koch Institute for Integrative Cancer Research, Massachusetts Institute of Technology, 500 Main Street, Cambridge, Massachusetts 02139, United States – name: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States |
| Author_xml | – sequence: 1 givenname: Timothy C surname: Adams fullname: Adams, Timothy C – sequence: 2 givenname: Joshua N surname: Payette fullname: Payette, Joshua N – sequence: 3 givenname: Jaime H surname: Cheah fullname: Cheah, Jaime H – sequence: 4 givenname: Mohammad surname: Movassaghi fullname: Movassaghi, Mohammad email: movassag@mit.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26336940$$D View this record in MEDLINE/PubMed |
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| Keywords | EPIPOLYTHIODIKETOPIPERAZINE ALKALOIDS ANTIBIOTICS GLIOTOXIN IN-VIVO TRIOXOPIPERAZINE PRECURSORS GENERAL-APPROACH CELL PROLIFERATION PREPARING EPIDITHIODIOXOPIPERAZINES ENANTIOSELECTIVE TOTAL-SYNTHESIS ARYL PYRROLOINDOLINES MESO-CHIMONANTHINE |
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| Snippet | The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a... |
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| SubjectTerms | Chemistry Chemistry, Organic Cyclization Diketopiperazines - chemical synthesis Diketopiperazines - chemistry Diketopiperazines - pharmacology Drug Screening Assays, Antitumor HeLa Cells Humans Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Indole Alkaloids - pharmacology Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Molecular Structure Physical Sciences Piperazines - chemical synthesis Piperazines - chemistry Piperazines - pharmacology Science & Technology Stereoisomerism |
| Title | Concise Total Synthesis of (+)-Luteoalbusins A and B |
| URI | http://dx.doi.org/10.1021/acs.orglett.5b02059 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000361087200037 https://www.ncbi.nlm.nih.gov/pubmed/26336940 https://search.proquest.com/docview/1709712453 https://pubmed.ncbi.nlm.nih.gov/PMC4597594 |
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