Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks.
This critical review showcases examples of rapid formation of complexity in total syntheses starting from 7-oxabicyclo[2.2.1]hept-5-ene derivatives. An overview of methods allowing synthetic access to these building blocks is provided and their application in recently developed synthetic transformations to structurally complex systems is illustrated. In addition, the facile access to a novel oxabicyclo[2.2.1]heptene derived building block is presented which significantly enlarges the possibilities of previously known chemical transformations and is highlighted in the enantioselective route to the core of the banyaside and suomilide natural products (107 references).
Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zuerich, Switzerland.
Corinna S
CS
Schindler
Erick M
EM
Carreira
D000475:Alkenes / Q000737:chemistry*; D053961:Azabicyclo Compounds; D001688:Biological Products / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D053961:Azabicyclo Compounds; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D006536:Heptanes; C533517:banyaside; C533518:suomilide