The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment
| Autor: | Linda E. Keown, Jose Luis Acena, Ian Paterson, Thomas Trieselmann, David Y.-K. Chen, Mark J. Coster, Jordi Bach |
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| Rok vydání: | 2005 |
| Předmět: |
Molecular Structure
Stereochemistry Chemistry Organic Chemistry Total synthesis Phosphonium salt Antineoplastic Agents Stereoisomerism Altohyrtin A Tetrahydropyran Biochemistry Spongistatin 1 chemistry.chemical_compound Kinetics Acetals Aldol reaction Alcohols Side chain Thermodynamics Spiro Compounds Macrolides Physical and Theoretical Chemistry Boron Pyrans |
| Zdroj: | Organicbiomolecular chemistry. 3(13) |
| ISSN: | 1477-0520 |
| Popis: | The fully functionalised C29–C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C–C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran. |
| Databáze: | OpenAIRE |
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