登入選單
返回Google圖書搜尋
Strategies and Tactics in Organic Synthesis
Michel MieschTania WelschVincent RietschLaurence Miesch
其他書名
Chapter 7. Total Syntheses of Hamigeran B
出版Elsevier Inc. Chapters, 2013-07-29
主題Science / Chemistry / Organic
ISBN012805610X9780128056103
URLhttp://books.google.com.hk/books?id=KjJ2DAAAQBAJ&hl=&source=gbs_api
EBookSAMPLE
註釋This chapter describes various syntheses of hamigeran B. Different methodologies were developed, and for our part, we achieved a formal synthesis of (±)-hamigeran B involving an intramolecular alkynylogous Mukaiyama aldol reaction promoted by dual Lewis acid activation as a key step. This unexpected reaction was discovered by treating a ketone with TBSOTf/NEt3 in order to obtain the corresponding silyl enol ether, which, in fact, evolves toward a new type of intramolecular aldol reaction. Fortunately, the study of the scope and limitations of this reaction allowed us to set up an original synthetic route to hamigeran B. Our results indicated clearly that serendipity plays a key role in the development of original strategies in organic synthesis.