Total synthesis of (+/-)-pallavicinin and (+/-)-neopallavicinin. ; CUHK electronic theses & dissertations collection

*Please refer to dissertation for diagrams. ; Chapter 2 is concerned with the aim of our research work, retrosynthetic analysis and strategy. Herein, we report the synthesis of the pivotal precursor aldehyde (112) by a Grob fragmentation procedure. In addition, model studies of the key biomimetic aldol cyclization are also discussed. We completed the total synthesis of the two novel diterpenes (+/-)-( 1) and (+/-)-(2) via intramolecular Michael reaction and alpha-ethylidenation starting from (+/-)-Wieland-Miescher ketone. ; In Chapter 1, an overview of the isolation, structure elucidation and bioactivities of pallavicinin (1) and neopallavicinin ( 2) are presented. In addition, various synthetic approaches toward the analogous skeletons of the two novel diterpenes are reviewed. ; In Chapter 3, a brief conclusion is provided.* ; Two novel diterpenes, named pallavicinin (1)and neopallavicinin (2)were first isolated from liverwort Pallavicinia subciliata by Wu16 and their coworkers in 1994. These compounds show potential bioactivities, such as antipyretic properties, muscle regeneration and detoxification.17,18 The diverse structural features of these novel diterpenes in conjunction with their potential bioactivities have stimulated our considerable interest in the quest for their total synthesis. ; Peng Xiahshui. ; "April 2006." ; Adviser: Henry N. C. Wong. ; Source: Dissertation Abstracts International, Volume: 67-11, Section: B, page: 6412. ; Thesis (Ph.D.)--Chinese University of Hong Kong, 2006. ; Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. ; Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. ; Abstracts in English and Chinese. ; School code: 1307.