2020
DOI: 10.1021/acs.orglett.0c03364
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Total Synthesis of (±)-Leonuketal

Abstract: Cleavage of a C-C bond is a diversifying process in the biogenesis of seco-terpenoids that has produced fascinating molecular structures. Leonuketal is an 8,9-seco-labdane terpenoid with a unique tetracyclic structure, owing to a C-C bond cleavage event in its biosynthesis. We report the first total synthesis of leonuketal, featuring an unusual Shapiro-type reaction as part of an enabling auxiliary ring strategy, and a novel Au-catalysed spirocyclisation of a -keto(enol)lactone. ASSOCIATED CONTENTSupporting I… Show more

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Cited by 7 publications
(4 citation statements)
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“…Our group has had a long-standing interest in spiroketal-containing natural products, due to their attractive bioactivities, ,, and the privileged nature of the spiroketal scaffold. We have accomplished the total synthesis of several spiroketal-containing natural products, including acortatarin A and pollenopyrroside A, which are structurally similar with 1 – 3 .…”
mentioning
confidence: 99%
“…Our group has had a long-standing interest in spiroketal-containing natural products, due to their attractive bioactivities, ,, and the privileged nature of the spiroketal scaffold. We have accomplished the total synthesis of several spiroketal-containing natural products, including acortatarin A and pollenopyrroside A, which are structurally similar with 1 – 3 .…”
mentioning
confidence: 99%
“…Additionally, 105 was subjected to in vitro cytotoxicity assays against four human cancer cell lines (A549, MCF‐7, HepG‐2 and MDA‐MB‐231) and displayed no activity [84] . The total synthesis of leonuketal ( 105 ) was achieved by Brimble and co‐workers in 2020 and is discussed in Section 3.14 [97, 98] …”
Section: Isolation and Bioactivitymentioning
confidence: 99%
“…reported the first total synthesis of leonuketal ( 105 ) by a strategy distinct from their preliminary investigations (Scheme 15 B). [97, 98] The synthesis commenced with the Ti III ‐mediated cyclisation of epoxide 275 to afford 276 with the formation of three chiral centres [136, 137] . Inversion of the C7 alcohol was then effected, delivering 277 , which served as the substrate for a pivotal Shapiro‐type reaction.…”
Section: Isolation and Bioactivitymentioning
confidence: 99%
“…3,5 Our group has had a longstanding interest in spiroketalcontaining natural products, due to their attractive bioactivities, 3,6,7 and the privileged nature [8][9][10] of the spiroketal scaffold. We have accomplished the total synthesis of several spiroketal-containing natural products, [11][12][13][14][15] including acortatarin A 16 and pollenopyrroside A, 17 which share structural similarities with 1-3. We were intrigued by the lycibarbarines because they appeared to represent kinetic [5,6]-and thermodynamic [6,6]spiroketal products derived from the same oxocarbenium precursor 4 (Scheme 1).…”
mentioning
confidence: 99%