Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds

Aluru Rammohan; Albert F Khasanov; Dmitry S Kopchuk; Duvvuru Gunasekar; Grigory V Zyryanov; Oleg N Chupakhin

doi:10.1007/s13659-022-00333-4

Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds

Nat Prod Bioprospect. 2022 Mar 31;12(1):12. doi: 10.1007/s13659-022-00333-4.

Authors

Aluru Rammohan^{1

2}, Albert F Khasanov^{3

4}, Dmitry S Kopchuk^{3

4}, Duvvuru Gunasekar⁵, Grigory V Zyryanov^{6

7}, Oleg N Chupakhin^{3

4}

Affiliations

¹ Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russian Federation. rammohan4ever@gmail.com.
² Natural Products Division, Department of Chemistry, Sri Venkateswara University, Tirupati, 517502, India. rammohan4ever@gmail.com.
³ Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russian Federation.
⁴ Ural Division of the Russian Academy of Sciences, I. Ya. Postovsky Institute of Organic Synthesis, 22 S. Kovalevskoy St., Ekaterinburg, 620219, Russian Federation.
⁵ Natural Products Division, Department of Chemistry, Sri Venkateswara University, Tirupati, 517502, India.
⁶ Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russian Federation. gvzyryanov@gmail.com.
⁷ Ural Division of the Russian Academy of Sciences, I. Ya. Postovsky Institute of Organic Synthesis, 22 S. Kovalevskoy St., Ekaterinburg, 620219, Russian Federation. gvzyryanov@gmail.com.

Abstract

The development of highly facile synthetic procedures for the expedient synthesis of complex natural molecules is always in demand. As this aspect, the Diels-Alder reaction (DAR) has a versatile approach to the synthesis of complex natural compounds and highly regio-/stereoselcetive heterocyclic scaffolds. Additionally, α-pyrone and terpenoquinone are two versatile key intermediates that are prevalent in various bioactive natural compounds for instance, (±)-crinine, (±)-joubertinamine, (±)-pancratistatin, (-)-cyclozonarone, and 8-ephipuupehedione, etc. Hence, the current review summarizes the Diels-Alder reaction application of α-pyrone and terpenoquinone to the constructive synthesis of various natural products over the past two decades (2001-2021). Equally, it serves as a stencil for the invention and development of new synthetic strategies for high-complex molecular structured natural and heterocyclic molecules.

Keywords: Diels–Alder reaction (DAR); Marine natural compounds; Terpenoquinone; Total synthesis; α-Pyrone.

Publication types

Review

Grants and funding

HШ-2700.2020.3/Council on grants of the President of the Russian Federation