Total synthesis of peloruside A via kinetic lactonization and relay RCM cyclization reactions (and identification of iso-peloruside A)
A convergent total synthesis of peloruside A ( 1 ) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C 2 -symmetric ketone 4 , which comprises C1–C9 of 1 , and a relay ring closing metathesis (RRCM) reaction to produce a dehydr...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2010-08, Vol.49 (35), p.6151-6155 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Hoye, Thomas R. Jeon, Junha Kopel, Lucas C. Ryba, Troy D. Tennakoon, Manomi A. Wang, Yini |
| description | A convergent total synthesis of peloruside A (
1
) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C
2
-symmetric ketone
4
, which comprises C1–C9 of
1
, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone
20
, which embodies C13–C19. A new isomer of
1
, the valerolactone
iso
-peloruside A (
iso
-1
), was identified. |
| doi_str_mv | 10.1002/anie.201002293 |
| format | Article |
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1
) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C
2
-symmetric ketone
4
, which comprises C1–C9 of
1
, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone
20
, which embodies C13–C19. A new isomer of
1
, the valerolactone
iso
-peloruside A (
iso
-1
), was identified.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201002293</identifier><identifier>PMID: 20645374</identifier><language>eng</language><ispartof>Angewandte Chemie International Edition, 2010-08, Vol.49 (35), p.6151-6155</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,777,781,882,27905,27906</link.rule.ids></links><search><creatorcontrib>Hoye, Thomas R.</creatorcontrib><creatorcontrib>Jeon, Junha</creatorcontrib><creatorcontrib>Kopel, Lucas C.</creatorcontrib><creatorcontrib>Ryba, Troy D.</creatorcontrib><creatorcontrib>Tennakoon, Manomi A.</creatorcontrib><creatorcontrib>Wang, Yini</creatorcontrib><title>Total synthesis of peloruside A via kinetic lactonization and relay RCM cyclization reactions (and identification of iso-peloruside A)</title><title>Angewandte Chemie International Edition</title><description>A convergent total synthesis of peloruside A (
1
) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C
2
-symmetric ketone
4
, which comprises C1–C9 of
1
, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone
20
, which embodies C13–C19. A new isomer of
1
, the valerolactone
iso
-peloruside A (
iso
-1
), was identified.</description><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqljz1PwzAURS0EouVjZX4jDCl2nDRhQUJVEQsL6m49HIc-cO3IdiuFH8DvxhUgwcz0rnSuztVj7ELwmeC8vEZHZlbyfS5v5AGbiroUhWwaeZhzJWXRtLWYsJMYX3Onbfn8mE1KPq9q2VRT9rHyCS3E0aW1iRTB9zAY68M2UmfgDnaE8EbOJNJgUSfv6B0TeQfoOgjG4ghPi0fQo7Y_JJhczCHC5b6URS5RT_qL5gWKvvi9cnXGjnq00Zx_31N2e79cLR6KYfu8MZ3OgoBWDYE2GEblkdRf4mitXvxO5ae4aBv5b8EnBgxydA</recordid><startdate>20100816</startdate><enddate>20100816</enddate><creator>Hoye, Thomas R.</creator><creator>Jeon, Junha</creator><creator>Kopel, Lucas C.</creator><creator>Ryba, Troy D.</creator><creator>Tennakoon, Manomi A.</creator><creator>Wang, Yini</creator><scope>5PM</scope></search><sort><creationdate>20100816</creationdate><title>Total synthesis of peloruside A via kinetic lactonization and relay RCM cyclization reactions (and identification of iso-peloruside A)</title><author>Hoye, Thomas R. ; Jeon, Junha ; Kopel, Lucas C. ; Ryba, Troy D. ; Tennakoon, Manomi A. ; Wang, Yini</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmedcentral_primary_oai_pubmedcentral_nih_gov_37401873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hoye, Thomas R.</creatorcontrib><creatorcontrib>Jeon, Junha</creatorcontrib><creatorcontrib>Kopel, Lucas C.</creatorcontrib><creatorcontrib>Ryba, Troy D.</creatorcontrib><creatorcontrib>Tennakoon, Manomi A.</creatorcontrib><creatorcontrib>Wang, Yini</creatorcontrib><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hoye, Thomas R.</au><au>Jeon, Junha</au><au>Kopel, Lucas C.</au><au>Ryba, Troy D.</au><au>Tennakoon, Manomi A.</au><au>Wang, Yini</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of peloruside A via kinetic lactonization and relay RCM cyclization reactions (and identification of iso-peloruside A)</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2010-08-16</date><risdate>2010</risdate><volume>49</volume><issue>35</issue><spage>6151</spage><epage>6155</epage><pages>6151-6155</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A convergent total synthesis of peloruside A (
1
) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C
2
-symmetric ketone
4
, which comprises C1–C9 of
1
, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone
20
, which embodies C13–C19. A new isomer of
1
, the valerolactone
iso
-peloruside A (
iso
-1
), was identified.</abstract><pmid>20645374</pmid><doi>10.1002/anie.201002293</doi></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2010-08, Vol.49 (35), p.6151-6155 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3740187 |
| source | Wiley Online Library - AutoHoldings Journals |
| title | Total synthesis of peloruside A via kinetic lactonization and relay RCM cyclization reactions (and identification of iso-peloruside A) |
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