Asymmetric Total Synthesis of Stagonolide G
A simple asymmetric total synthesis of stagonolide G (1) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard reactions are involved in generating the stereogenic centers C(4) and C(8), followed by Grubbs‐II‐catalyzed ring‐closing metathesis (RCM).
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| Published in: | Helvetica chimica acta Vol. 94; no. 7; pp. 1226 - 1233 |
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| Main Authors: | , , , , , |
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Zürich
WILEY-VCH Verlag
01-07-2011
WILEY‐VCH Verlag |
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| Abstract | A simple asymmetric total synthesis of stagonolide G (1) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard reactions are involved in generating the stereogenic centers C(4) and C(8), followed by Grubbs‐II‐catalyzed ring‐closing metathesis (RCM). |
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| AbstractList | A simple asymmetric total synthesis of stagonolide G (
1
) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl
Grignard
reactions are involved in generating the stereogenic centers C(4) and C(8), followed by
Grubbs‐II‐
catalyzed ring‐closing metathesis (RCM). A simple asymmetric total synthesis of stagonolide G (1) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard reactions are involved in generating the stereogenic centers C(4) and C(8), followed by Grubbs‐II‐catalyzed ring‐closing metathesis (RCM). |
| Author | Ramesh, Dasari Venkateswarlu, Yenamandra Rajaram, Singanaboina Ramulu, Udugu Kumar Reddy, Dorigondla Prabhakar, Peddikotla |
| Author_xml | – sequence: 1 givenname: Dasari surname: Ramesh fullname: Ramesh, Dasari organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) – sequence: 2 givenname: Singanaboina surname: Rajaram fullname: Rajaram, Singanaboina organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) – sequence: 3 givenname: Peddikotla surname: Prabhakar fullname: Prabhakar, Peddikotla organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) – sequence: 4 givenname: Udugu surname: Ramulu fullname: Ramulu, Udugu organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) – sequence: 5 givenname: Dorigondla surname: Kumar Reddy fullname: Kumar Reddy, Dorigondla organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) – sequence: 6 givenname: Yenamandra surname: Venkateswarlu fullname: Venkateswarlu, Yenamandra email: luchem@iict.res.in organization: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India , (phone: +91-40-27193167; fax: +91-40-27160512) |
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| CitedBy_id | crossref_primary_10_1016_j_tetasy_2012_01_014 crossref_primary_10_1016_j_tetasy_2015_07_007 crossref_primary_10_1002_hlca_201400200 crossref_primary_10_1002_hlca_201400265 crossref_primary_10_1016_j_tetlet_2022_154081 crossref_primary_10_1016_j_tetlet_2011_12_122 crossref_primary_10_1016_j_tetlet_2012_03_098 crossref_primary_10_1016_j_ccr_2013_05_011 crossref_primary_10_1016_j_tetasy_2014_09_009 crossref_primary_10_1016_j_tetlet_2013_11_071 |
| Cites_doi | 10.1016/j.tetasy.2010.01.010 10.1021/np0703038 10.1021/jo9823893 10.1021/jf070742c 10.1016/S0040-4039(00)80713-3 10.1007/s11418-008-0246-z 10.1016/j.bmc.2008.10.089 10.1039/np9971400453 10.1016/j.tetlet.2009.12.038 10.1021/jo982130k 10.1016/j.tet.2009.01.101 10.1021/jo981316g 10.1016/S0040-4039(98)02561-1 10.1080/10286020902942350 10.1021/np800415w 10.1016/S0040-4020(01)87445-7 10.1016/j.bioorg.2008.12.002 10.1002/hlca.200900068 10.1021/cr050045o 10.1016/j.tetlet.2010.03.102 10.1016/S0957-4166(97)00348-0 10.1002/(SICI)1522-7189(199809/10)6:5<183::AID-NT23>3.0.CO;2-U 10.1016/j.tetasy.2009.03.034 10.1039/B703499G 10.1016/j.tetasy.2009.09.016 10.1021/ol049696h |
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| Snippet | A simple asymmetric total synthesis of stagonolide G (1) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard... A simple asymmetric total synthesis of stagonolide G ( 1 ) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl Grignard... |
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| SubjectTerms | Dihydroxylation Epoxide opening Grignard reaction Ring-closing methathesis Stagonolide G |
| Title | Asymmetric Total Synthesis of Stagonolide G |
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