The C29-C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and D-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29-C37 vinyl bromide and the C38-C44 Weinreb amide, diastereoselective reduction of the C38 ketone, and
Synthetic studies on altohyrtins (spongistatins): synthesis of the C15–C28 (CD) spiroacetal portion
✍ Scribed by Takeshi Terauchi; Taro Terauchi; Ippei Sato; Tomoharu Tsukada; Naoki Kanoh; Masaya Nakata
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 266 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The C15-C28 portion of altohyrtins (spongistatins) was prepared in a convergent manner from methyl (S)-3hydroxy-2-methylpropionate, D-arabitol, and diacetone-D-glucose via dithiane couplings with epoxides as the key segment coupling process.
📜 SIMILAR VOLUMES
The C! 6-C28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration.
A convergent synthesis of the C29-C44 fragment, the common subunit of the spongipyran macrolides is described. The key step of the synthesis is the C-glycosidation reaction which is based on coupling of the lithiated F-ring sulfone with the E-ring aldehyde, and subsequent reductive desulfonylation t