TOTAL SYNTHESES OF BERGAMOTANE SESQUITERPENES AND LYCOPODIUM ALKALOIDS AND COMPUTATIONAL STUDY TOWARD DIAMINATION OF ALLENES AND [2+2] SELECTIVITY

Total synthesis of massarinolin A, purpurlides B, D, E, 2,3-deoxypurpurolide C, phleghenrines A and B were finished. A halogen bond promoted michael addiation was discovered during mechanism study toward diamination of allenes. Computational chemsitry study conducted toward the selectivity of 2+2 reaction supported the proposed key reaction during total synthesis of gibberellic acid 18.