Total Synthesis of the Marine Metabolite (−)-Clavosolide D
The first total synthesis of the marine natural product (−)-clavosolide D is described confirming the structure of the unsymmetrical 16-membered diolide glycosylated by permethylated d-xylose moieties. Following efficient assembly of the two tetrahydropyrans using stereoselective Prins cyclizations,...
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| Veröffentlicht in: | Organic letters 2008-04, Vol.10 (8), p.1637-1640 |
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| container_title | Organic letters |
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| creator | Seden, Peter T Charmant, Jonathan P. H Willis, Christine L |
| description | The first total synthesis of the marine natural product (−)-clavosolide D is described confirming the structure of the unsymmetrical 16-membered diolide glycosylated by permethylated d-xylose moieties. Following efficient assembly of the two tetrahydropyrans using stereoselective Prins cyclizations, the side chains were introduced via an allylation/isomerization/anti cyclopropanation sequence; the final macrolactonization step was achieved under Yamaguchi conditions. |
| doi_str_mv | 10.1021/ol800386d |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2008-04, Vol.10 (8), p.1637-1640 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70490012 |
| source | MEDLINE; American Chemical Society (ACS) Journals |
| subjects | Animals Cyclization Macrolides - chemical synthesis Macrolides - chemistry Marine Biology Models, Molecular Porifera |
| title | Total Synthesis of the Marine Metabolite (−)-Clavosolide D |
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