Asymmetric Formal Total Syntheses of (+)- and (-)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder Reaction

Asymmetric Formal Total Syntheses of (+)- and (−)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder Reaction
  • Oh, Sang-Ha
  • Oh, Joo-Yeon
  • Vo, Ngoc Binh
  • Ngo, Quoc Anh
  • Kovalenko, Vitaly
  • ... Cho, Cheon-Gyu
Citations

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SCOPUS

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초록

A new asymmetric synthetic route to (+)- and (−)-limaspermidine was devised, starting with chirally resolved enantiomerically pure 2-pyrone Diels–Alder cycloadducts. This route utilizes intramolecular Pd-catalyzed aromatic C–H amidation and imino-Diels–Alder reactions to construct the key indoline and indolizidine subunits onto the central cyclohexane core, allowing the straightforward formal total syntheses of both (+)- and (−)-limaspermidine.

키워드

ALKALOIDSCHEMISTRYINDOLINESNITRILESSTRATEGY
제목
Asymmetric Formal Total Syntheses of (+)- and (-)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder Reaction
제목 (타언어)
Asymmetric Formal Total Syntheses of (+)- and (−)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder Reaction
저자
Oh, Sang-HaOh, Joo-YeonVo, Ngoc BinhNgo, Quoc AnhKovalenko, VitalyCho, Cheon-Gyu
DOI
10.1021/acs.joc.4c01696
발행일
2024-09
유형
Article
저널명
Journal of Organic Chemistry
89
18
페이지
13501 ~ 13510