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Prins Cyclization |
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| The Prins reaction between a homoallylic alcohol and an aldehyde in acidic solution is a well established synthesis of tetrahydropyrans. These reactions can be regioselective and stereoselective which allows easier access to natural products containing tetrahydropyrans. |
Autumn Maruniak |
Megan Bolla |
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Reductive Decyanation |
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| A nitrile alkylation performed on a tetrahydropyran ring has the capability of setting up a highly functionalized precursor for a powerful annulation reaction. A reductive cyclization of these precursors gives spirocycles, in some cases, with excellent stereoselectivity. In some cases, this intramolecular cyclization gives quaternary centers. |
Rob Bahde Brian Slafer |
Matt Morin V. Malathong Justin Leong |
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Chiral Auxiliaries for Oxocarbenium Ion Reactions |
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| An α-trimethylsilyl benzyl group serves as an excellent chiral auxiliary for reactions proceeding via oxocarbenium ion intermediates. The alcohols formed using the auxiliary are optically pure and can remain protected as the benzyl group or can be deprotected efficiently. |
John Huckins |
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| Natural Product Synthesis | |||
| Natural product synthesis is an integral part of the Rychnovsky lab. The mechanistic studies and methodology listed above directly apply to the natural products our group is interested in synthesizing. Some molecules that we have synthesized or made progress towards are as follows: |
All Members of the Rychnovsky Group |
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| (-)-elisapterosin B | SCH-351448 | ||
| (+)-combrestatin D-1 | (-)-colombiasin A | ||
| phorboxazole B | (±)-laurenan | ||
| (-)-centrolobine | filipin III | ||
| (-)-roxaticin | dermostatin A | ||
| roflamycoin | 17-deoxyroflamycoin | ||
| leucascandrolide A | combrestatin D-2 | ||
| ent-cholesterol | (-)-apicularen A | ||
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rimocidin |
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