Total Synthesis of PF1163B

Abstract A total synthesis of PF1163B has been achieved. The vinylogous Mukaiyama aldol reaction of ketene silyl N , O -acetal 6 ( ent - 6 ) mediated by excess TiCl 4 proceeded with saturated aldehydes to give adduct 10 in moderate yield with moderate stereoselectivity. The major isomer is the diast...

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Bibliographic Details
Published in:Synlett 2019-04, Vol.30 (6), p.709-712
Main Authors: Sengupta, Aakash, Hosokawa, Seijiro
Format: Article
Language:English
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Summary:Abstract A total synthesis of PF1163B has been achieved. The vinylogous Mukaiyama aldol reaction of ketene silyl N , O -acetal 6 ( ent - 6 ) mediated by excess TiCl 4 proceeded with saturated aldehydes to give adduct 10 in moderate yield with moderate stereoselectivity. The major isomer is the diastereomer that was provided by using one equivalent of TiCl 4 . The Birch reduction of α,β-unsaturated imide 4 , possessing a less hindered side chain, gave 12 in good stereoselectivity by employing 2-isopropylbenzimidazole as a bulky proton source. After elongation of the carbon chain and connection with the amino acid part, we accomplished a total synthesis of PF1163B. These methods constitute a concise synthetic route to obtain polyketides as well as depsipeptides.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1610694