Stereoselective Synthesis of Both Tetrahydropyran Rings of the Antitumor Macrolide, (−)-Lasonolide A
✍ Scribed by Ghosh, Arun K.; Ren, Guo-Bao
- Book ID
- 115474295
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 554 KB
- Volume
- 77
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
The C 15 -C 25 upper THP segment 2 of (+)-lasonolide A has been synthesized efficiently via diastereomeric differentiation, iodocyclization and Julia-Kocien ´ski's sulfone olefination to install its quaternary chiral center, cis-2,6-disubstituted THP and trans-olefin, respectively.
A stereoselective synthesis of the C 17 ±C 28 segment of the potent antitumor macrolide, laulimalide has been accomplished. The key steps are a ring-closing ole®n metathesis to construct the dihydropyran unit, nucleophilic addition of an alkynyl anion to the Weinreb amide, stereoselective reduction