Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketals
TL;DR: In this paper, the authors reactite des boranes du titre vis-a-vis du clivage d'acetals cycliques et acycliques, de cetals, de perhydropyrannyl-and perhydrofuryl ethers, de glycosides de methyle, d'acetonides and d'ethers de -methoxymethyle, -methyl-methoxyethoxyl methyl and methylthiomethyle
Abstract: Reactivite des boranes du titre vis-a-vis du clivage d'acetals cycliques et acycliques, de cetals, de perhydropyrannyl- et perhydrofuryl ethers, de glycosides de methyle, d'acetonides, d'ethers de -methoxymethyle, -methoxyethoxymethyl et methylthiomethyle
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TL;DR: This data indicates that the phytochemical properties of Aplysiatoxin-like substances have changed significantly since their discovery in the 1970s, and these changes have implications for the design of new drugs and their application in medicine.
Abstract: 1. Intoduction 4348 2. Oxolane Macrodiolides 4348 2.1. Pamamycin 607 (1) 4348 2.1.1. Thomas Total Synthesis20 4349 2.1.2. Lee Total Synthesis28 4351 2.1.3. Metz Total Synthesis35 4353 2.1.4. Kang Total Synthesis41 4354 2.2. Amphidinolide X (2) 4356 2.2.1. Fürstner Total Synthesis59 4356 3. Oxane/Oxene Macrodiolides 4359 3.1. SCH 351448 (3) 4359 3.1.1. Lee Total Synthesis71 4359 3.2. Swinholide A (4) 4360 3.2.1. Paterson Total Synthesis82 4360 3.2.2. Nicolaou Total Synthesis83 4360 4. Cyclic Acetal Macrodiolides 4362 4.1. Cycloviracin B1 (5) 4362 4.1.1. Fürstner Total Synthesis96 4363 4.2. Glucolipsin A (6) 4366 4.2.1. Fürstner Total Synthesis117 4366 5. Cyclic Hemiketal Macrodiolides 4368 5.1. Boromycin (7) 4368 5.1.1. White Total Synthesis123 4368 5.2. Tartrolon B (8) 4369 5.2.1. Mulzer Total Synthesis130 4370 5.3. Debromoaplysiatoxin (9) and Aplysiatoxin (10) 4373 5.3.1. Kishi Total Synthesis142 4373 6. Conclusions 4375 7. Acknowledgments 4375 8. References 4375
256 citations
TL;DR: In this article, the authors treated carbohydrate acetals and dithioacetals with a dilute solution of iodine in methanol and provided a simple, convenient, and high yielding process for cleavage of the acetal functions.
147 citations
TL;DR: Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselectives hydrogenation of a fully substituted conjugated diene ester.
Abstract: The total synthesis of the architecturally complex Daphniphyllum alkaloid (−)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels–Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester.
106 citations