Total synthesis of (±)-otonecine, a necine base of pyrrolizidine alkaloids
✍ Scribed by Haruki Niwa; Youchi Uosaki; Kiyoyuki Yamada
- Book ID
- 104226341
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 130 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
&one&z (l_), a hepfitinenAative necine base ad hepatoLotic and catroinog~tic py~~~oLLz~&ne aLkaLoL&, ~a6 nyntienized -in ~~~cemic dam #om eXhq1 I-hydtloxy-2,3,5,6-&&ahq&o-TH-pqwcoLLz~iu-7-catrboxy~~e (21.
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Molecular mechanics calculations were applied to the Ž . conformational analysis of two diasteroisomers, the pyrrolizidine alkaloids PAs retronecine and heliotridine. The application of reoptimized parameters for H Ž . bonding corrected the tendency of MM3 92 calculations to give unrealistic H иии O
The total synthesis of the potent glycosidase inhibitor (+)-alexine with five contiguous stereogenic centres [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine alkaloid] is described featuring the efficient and stereodefined novel elaboration of the functionalized homochiral lactam der