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Spirastrellolide studies. Synthesis of the C(1)-C(25) southern hemispheres of spirastrellolides A and B, exploiting anion relay chemistry |
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| Authors: | Amos B. Smith III Helmars Smits Dae-Shik Kim |
| Affiliation: | Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, 231 South 34th St., Philadelphia, PA 19104, USA |
| Abstract: | Construction of the C(1)-C(25) southern fragments of both spirastrellolide A and B are described. Highlights of the syntheses include effective use of the three component anion relay chemistry (ARC) tactic recently introduced by our laboratory, a stereoselective spirocyclization via concomitant Ferrier reaction to elaborate the BC spiroketal and use of two dithiane unions to install the A ring as well as C(22)-C(25) fragment. The synthesis proceeded with longest linear sequences of 33 and 32 steps, respectively for spirastrellolide A and spirastrellolide B. |
| Keywords: | Spirastrellolide Anion relay chemistry Brook rearrangement Stereoselective Spirocyclization Petasis-Ferrier reaction Dithiane Multicomponent reaction Spiroketal Natural product Polyketide Total synthesis |
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