P-73 プルヌスタチンAの合成研究(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • Synthetic Studies on Prunustatin A

抄録

Prunustatin A (1), was isolated from a strain of Streptomyces violaceoniger 4521-SVS3 by Shin-ya and co-workers in 2005, and showed inhibitory activity against GRP78 expression induced by 2-deoxyglucose stimulation in HT1080 cells. We have been interested in establishing the structure-activity relationship of 1, and engaged in studies toward the total synthesis of 1. We have planed to construct the tetralactone ring of 1 via intramolecular Mitsunobu reaction of 2a, which would be prepared by esterification of carboxylic acid 3 with alcohol 4. We first attempted to prepare 3 by esterification between alcohol 9 and carboxylic acid 10, which was syn-selectively synthesized via Mukaiyama aldol reaction of aldehyde 6, derived from L-phenylalanine, with silyl enolether 17. However, the desired esterification would not proceed at all, which were presumably due to the steric hindrance of the quaternary carbon adjacent to the carbonyl group of 10. We next forced on the C-C bond formation reaction between C1 and C11 via Reformatsky reaction. Under optimized condition, the reaction of aldehyde 6 with α-bromoester 5 proceeded successfully to afford 3 in 82% yield. The following esterification of 4 and hydrogenolysis provided the ring-closing precursor 2a in 65% yield.

収録刊行物

詳細情報

  • CRID
    1390001206077422208
  • NII論文ID
    110009757801
  • DOI
    10.24496/tennenyuki.52.0_457
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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