1. Progress toward the synthesis of vancosamine using a tandem [4+2]/[3+2] cycloaddition. 2. Discussion boards and pre-lecture quizzes in organic chemistry courses

The sugar vancosamine is one of the two sugar residues found on the broad spectrum antibiotic vancomycin. A strategy using a tandem intermolecular [4+2]/intermolecular [3+2] cycloaddition with nitro olefins was employed in an effort to enantioselectively synthesize the target. The [4+2] cycloaddition proceeded well with tin tetrachloride in high yield. However, the products from the [3+2] cycloaddition afforded diastereomers with stereocenters that were inconsistent with the natural product.; An online facilitated group work assignment was introduced to a first semester non-majors organic chemistry lecture courses with large enrollments (∼300--660 students). Student opinion surveys, performance scores, and a detailed account of time spent by the facilitator afforded insight on the value of such assignments with large class sizes.; Format and number of attempts were varied in online pre-lecture quizzes administered to a first semester non-majors organic chemistry lecture course. Student quiz performance and post-quiz assessment shows significant differences in mastery of material and class preparedness with format and number of attempts. When combined with student survey data, recommendations are made as to how format selection and number of attempts can optimize the value of online pre-lecture quizzes as a learning tool and as an assessment tool.