A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids
نویسنده
چکیده
This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidines: (-)-indolizidines 167B, 195B, 223AB, (+)-monomorine, (-)-(3R,5S,8aS)-3-butyl-5-propylindolizidine and (-)-dendroprimine. Next, we relate the synthesis that we have developed in the quinolizidines field: (+/-)-myrtine and epimyrtine, (+/-)-lasubines I and II and chiral quinolizidines: (+)-myrtine, (-)-epimyrtine, (-)-lasubines I and II and (+)-subcosine II.
منابع مشابه
Total synthesis of the indolizidine alkaloid tashiromine
BACKGROUND Tashiromine 1 is a naturally occurring indolizidine alkaloid. It has been the subject of thirteen successful total syntheses to date. Our own approach centres on the stereoselective construction of the indolizidine core by capture of an electrophilic acyliminium species by a pendant allylsilane. The key cyclisation precursor is constructed using olefin cross-metathesis chemistry, whi...
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عنوان ژورنال:
- Beilstein Journal of Organic Chemistry
دوره 3 شماره
صفحات -
تاریخ انتشار 2007