Total synthesis of a diastereomer of the marine natural product clavosolide A
- PMID: 16220183
- DOI: 10.1039/b509757f
Total synthesis of a diastereomer of the marine natural product clavosolide A
Abstract
The first total synthesis of the reported structure of the sponge metabolite clavosolide A is described using a Prins cyclisation to assemble the tetrahydropyran core followed by manipulation of the side-chain, dimerisation and finally glycosidation.
Similar articles
-
Total synthesis of the marine natural product (-)-clavosolide A.Org Lett. 2006 Jul 20;8(15):3319-22. doi: 10.1021/ol0611705. Org Lett. 2006. PMID: 16836395
-
Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic.Org Lett. 2006 Jul 20;8(15):3315-8. doi: 10.1021/ol0611752. Org Lett. 2006. PMID: 16836394
-
An efficient formal synthesis of (-)-clavosolide a featuring a "mismatched" stereoselective oxocarbenium reduction.Org Lett. 2009 Feb 5;11(3):769-72. doi: 10.1021/ol8028302. Org Lett. 2009. PMID: 19125666
-
Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.Chem Rev. 2005 Dec;105(12):4779-807. doi: 10.1021/cr040632u. Chem Rev. 2005. PMID: 16351062 Review. No abstract available.
-
Total synthesis of oxacyclic macrodiolide natural products.Chem Rev. 2005 Dec;105(12):4348-78. doi: 10.1021/cr040629a. Chem Rev. 2005. PMID: 16351047 Review. No abstract available.
Cited by
-
Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.Chemistry. 2016 Jun 6;22(24):8158-66. doi: 10.1002/chem.201600674. Epub 2016 May 3. Chemistry. 2016. PMID: 27139508 Free PMC article.
-
Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction.Tetrahedron Lett. 2015 Jun 3;56(23):3120-3122. doi: 10.1016/j.tetlet.2014.11.135. Tetrahedron Lett. 2015. PMID: 26236051 Free PMC article.
-
Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10718-10722. doi: 10.1002/anie.201906259. Epub 2019 Jun 24. Angew Chem Int Ed Engl. 2019. PMID: 31166641 Free PMC article.
-
Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.Org Lett. 2012 Nov 2;14(21):5614-7. doi: 10.1021/ol302744t. Epub 2012 Oct 24. Org Lett. 2012. PMID: 23095114 Free PMC article.
-
Racemization in Prins cyclization reactions.J Am Chem Soc. 2006 Oct 18;128(41):13640-8. doi: 10.1021/ja064783l. J Am Chem Soc. 2006. PMID: 17031979 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources