Abstract
The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.
Original language | English |
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Article number | st-2015-u0570-l |
Pages (from-to) | 2437-2441 |
Number of pages | 5 |
Journal | Synlett |
Volume | 26 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2015 Oct 22 |
Keywords
- aflastatin A
- aldol reactions
- carbohydrates
- polyols
- stereoselectivity
ASJC Scopus subject areas
- Organic Chemistry