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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 7: 2820 - 2830

DOI: https://doi.org/10.6023/cjoc202102021

ARTICLES

Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

  • Qi Yu ,
  • Shuai Yang ,
  • Congyun Tang ,
  • Lin Peng ,
  • Zhili Zuo ,
  • Liangliang Wang
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  • a School of Food and Chemical Engineering, Shaoyang University, Shaoyang, Hunan 422000
    b State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201
* Corresponding authors. E-mail: ;
;

Received date: 2021-02-06

  Revised date: 2021-03-30

  Online published: 2021-04-06

Supported by

“Light of West China” Program; Youth Innovation Promotion Association of the Chinese Academy of Sciences; National Natural Science Foundation of China(21772207); “Thousand Talents Program” of Yunnan Province; Program from Education Department of Hunan Province(19c1655)

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Abstract

The Elansolid A1/A2 is metabolite from the gliding bacteriumChitinophaga sanctiiand shows antibiotic activity against Gram-positive bacteria. Up to now, the total synthesis of this natural product has not been reported yet due to its structure complexity, which arises from thetrans-tetrahydroindane unit and (Z)-(E)-(Z) triene motif as well as a 19-member macrolactone. In this study, two newO-functionalized substrates were synthesized to undergo the biomimetic intramolecular Diels-Alder reactions (IMDA) catalyzed by a chiral phosphoric acid to build the keytrans-tetrahydroindane core of Elansolid A1/A2 via a vinylicp-quinone methide intermediate. This result shows that an improveddr (1.8∶1) of IMDA reaction and shorter synthetic steps could be achieved.

Key words： biomimetic synthesis; Diels-Alder reaction; tetrahydroindane; elansolid

Cite this article

Qi Yu , Shuai Yang , Congyun Tang , Lin Peng , Zhili Zuo , Liangliang Wang . Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2820 -2830 . DOI: 10.6023/cjoc202102021

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