Stereocontrolled Carbocyclic Construction - -Mintlactone Bates , -Gleenol Kobayashi , - -Vibralactone C Snider

Nigel S. Simpkins, now at the University of Birmingham, found (Chem. Commm. 2008, 5390) that the prochiral cyclopropane amide 1 could be deprotonated to give, after alkylation, the substituted cyclopropane 3 with high enanantio- and diastereocontrol. In the course of a synthesis of (-l-)-Lineatin, Ramon Abbes of the Universitat Autonoma de Barcelona optimized (J. Org. Chem 2008, 73, 5944) the photochemical cycloaddition of 4 and 5 to give, after reductive dechlorination, the cyclobutene 6. 

Roderick W. Bates of Nanyang Technological University found (J. Org. Chem. 2008, 73, 8104), in a synthesis of (-)-Mintlactone 29, that the diastereocontroUed reductive cyclization of 27 to 28 worked best in wet DMF. Susianu Kobayashi of the Tokyo University of Science showed (Chemistry Lett. 2008, 37, 770), en route to (-)-Gleenol 32, that the Claisen rearrangement of 30 deUvered the cyclohexene 31 with high diastereocontrol. Barry B. Snider of Brandeis University prepared (J. Org. Chem. 2008, 73, 8049) (-)-Vibralactone C 36 from 33, available from o-anisic acid by the Schultz protocol. 

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