A divergent approach to apoptolidin and FD-891: asymmetric preparation of a common intermediate
β Scribed by Shu-Sin Chng; Jia Xu; Teck-Peng Loh
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 395 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Biologically active Apoptolidin and FD-891 have structural similarity in their macrocyclic cores. Asymmetric preparation of a common intermediate in the total synthesis of these two macrolides is presented. A modified Masuyama Sn-allylation was employed to control the relative stereochemistry in the synthesis of the intermediate.
π SIMILAR VOLUMES
## Abstract Malonate diesters containing a prochiral quaternary carbon have been successfully transformed into analogs of cysteine and serine. The chiral halfβesters are obtained in good yield, and enantioselectivity by selective hydrolysis using PigβLiver Esterase (PLE) as the catalyst. The result
The title compounds were synthesized from a readily available steroidal acetylene by a protocol employing selenosulfonation, introduction of the appropriate side chain at C-24 via an alkyl selenocuprate, and reductive desulfonylation. A similar elimination has been observed in the reaction of the s