Enantioselektive Totalsynthese des Diterpens (+)‐Cubiten

Simon, Kristina; Wefer, Johannes; Schöttner, Elisabeth; Lindel, Thomas

doi:10.1002/ange.201205143

Cited by 7 publications

(1 citation statement)

References 32 publications

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“…8,9 Still, although a total synthesis of calyculone A ( 2 ) and its derivatives has remained elusive, thus far only one group has described an approach toward its core ring system. 10 Although calyculone A ( 2 ) has displayed substantial cytotoxicity, 6 as it happens with many marine natural products, the lack of an adequate supply of material has impeded research into the biological potential of the calyculones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological analysis of truncated calyculone H

Balasubramanyam

Rodrı́guez

2017

Tetrahedron

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Herein, we report for the first time the design and linear synthesis of a truncated calyculone H (7) that lacks the telltale isopropyl/isopropylene groups, whereas the 12-membered macrocycle remains intact. Key steps for the framework of target molecule include allylic oxidation using SeO2, Sharpless asymmetric epoxidation, Barbier zinc allylation, and ring-closing metathesis (RCM) reactions. A second truncated “calyculone-like” analogue, 27, with a different oxidation pattern around the ring was also synthesized following a similar strategy. Screening for in vitro cytotoxicity against a panel of 60 human cancer cell lines revealed that 7 was as potent if not more so (for a few cell lines) than the natural product calyculone A (2).

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological analysis of truncated calyculone H

Balasubramanyam

Rodrı́guez

2017

Tetrahedron

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A General Entry to Antifeedant Sesterterpenoids: Total Synthesis of (+)‐Norleucosceptroid A, (−)‐Norleucosceptroid B, and (−)‐Leucosceptroid K

Hugelshofer¹,

Magauer²

2014

Angewandte Chemie

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The first asymmetric total synthesis of the antifeedant terpenoids (+)‐norleucosceptroid A, (−)‐norleucosceptroid B, and (−)‐leucosceptroid K has been accomplished. This highly concise synthetic route was guided by our efforts to develop a platform for the collective synthesis of a whole family of antifeedant natural products. The synthesis features a Hauser–Kraus‐type annulation followed by an unprecedented, highly efficient intramolecular dilactol aldol‐type condensation reaction to produce the 5,6,5 skeleton. The developed synthetic route proceeds for norleucosceptroid A and B in 16 steps (longest linear sequence) from known compounds.

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Total Synthesis of Leucosceptroids A and B

Guo

Liu

2014

Angewandte Chemie

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Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram‐scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)‐citronellal‐derived aldehyde, a SmI2‐mediated intramolecular ketyl–olefin radical cyclization, and final‐stage alcohol oxidation.

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Enantioselektive Totalsynthese des Diterpens (+)‐Cubiten

Cited by 7 publications

References 32 publications

Synthesis and biological analysis of truncated calyculone H

Synthesis and biological analysis of truncated calyculone H

A General Entry to Antifeedant Sesterterpenoids: Total Synthesis of (+)‐Norleucosceptroid A, (−)‐Norleucosceptroid B, and (−)‐Leucosceptroid K

Total Synthesis of Leucosceptroids A and B

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