Polyhydroxylated indolizidine alkaloids—an efficient synthesis of 1-deoxy-8,8a-di-epi-castanospermine
نویسندگان
چکیده
منابع مشابه
Polyhydroxylated indolizidine alkaloids—an efficient synthesis of 1-deoxy-8,8a-di-epi-castanospermine
A new and efficient enantioselective total synthesis of the title deoxycastanospermine derivative has been developed, based on amino acid and b-ketophosphonate chemistry, as well as employment of internal asymmetric induction for the creation of the new chiral centers proved successful. With proper choice of reaction conditions, the approach can also be applied in selective preparation of sever...
متن کاملAsymmetric total synthesis of 1-deoxy-7,8-di-epi-castanospermine.
An efficient, stereocontrolled synthesis of (6S,7S,8S,8aR)-6,7,8-trihydroxyindolizidine (alias 1-deoxy-7,8-di-epi-castanospermine) (14) has been developed, which exploits an asymmetric vinylogous Mukaiyama aldol reaction (VMAR) between N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)pyrrole (1) and 2,3-O-isopropylidene-D-glyceraldehyde (2) to construct the initial pyrrolidine building blo...
متن کاملAsymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine.
Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring ex...
متن کاملPolyhydroxylated indolizidine alkaloids-synthesis of dideoxycastanospermine
Powered by TCPDF (www.tcpdf.org) This material is protected by copyright and other intellectual property rights, and duplication or sale of all or part of any of the repository collections is not permitted, except that material may be duplicated by you for your research use or educational purposes in electronic or print form. You must obtain permission for any other use. Electronic or print cop...
متن کاملPolyhydroxylated indolizidine alkaloidsdsynthesis of dideoxycastanospermine
Powered by TCPDF (www.tcpdf.org) This material is protected by copyright and other intellectual property rights, and duplication or sale of all or part of any of the repository collections is not permitted, except that material may be duplicated by you for your research use or educational purposes in electronic or print form. You must obtain permission for any other use. Electronic or print cop...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Tetrahedron
سال: 2003
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00918-9