ArticleThe Journal of organic chemistry2011
Total synthesis of dolabelide C: a phosphate-mediated approach.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Ring-Opening Reactions of Phosphoramidate Heterocycles.Tetrahedron · 2023Article
- E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.Nature chemistry · 2022Article
- Trisubstituted triumph.Nature chemistry · 2022Article
- Bioactive Compounds from Marine Heterobranchs.Marine drugs · 2020Review
- Marine Mollusk-Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance.Medicinal research reviews · 2017Review
- Synthesis of the C9-C25 Subunit of Spirastrellolide B.Organic letters · 2016Article
- Modular Synthesis of Novel Macrocycles Bearing α,β-Unsaturated Chemotypes through a Series of One-Pot, Sequential Protocols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.The Journal of organic chemistry · 2016Article
- A Pot-Economical Approach to the Total Synthesis of Sch-725674.Organic letters · 2016Article
- Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large,Tetrahedron · 2015Article
- Synthetic Studies to Lyngbouilloside: A Phosphate Tether-Mediated Synthesis of the Macrolactone Core.Tetrahedron letters · 2015Article
- A modular phosphate tether-mediated divergent strategy to complex polyols.Beilstein journal of organic chemistry · 2014Article
- Phosphate-tether-mediated ring-closing metathesis for the preparation of complex 1,3-anti-diol-containing subunits.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- A phosphate tether-mediated, one-pot, sequential ring-closing metathesis/cross-metathesis/chemoselective hydrogenation protocol.Organic letters · 2012Article
- Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed Prins cyclizations.Angewandte Chemie (International ed. in English) · 2011Article
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Authors and funding
6 authors.
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Abstract
The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S(P))-5 and (R,R,R(P))-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
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