Convergent biomimetic semisynthesis of disesquiterpenoid rumphellolide J-Reference-Cited by-同舟云学术

Convergent biomimetic semisynthesis of disesquiterpenoid rumphellolide J

Published:2022 Issue:12 Volume:20 Page:2455-2461
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Stakanovs Georgijs¹,Belyakov Sergey¹,Jirgensons Aigars¹^ORCID,Rasina Dace¹^ORCID

Affiliation:

1. Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006, Riga, Latvia

Abstract

The gram-scale synthesis of disesquiterpenoid ester rumphellolide J (5) from (−)-β-caryophyllene (1) and (−)-caryophyllene oxide (3) via natural products 4β,8β-epoxycaryophyllan-5-ol (2) and (+)-rumphellaoic acid A (4) is demonstrated.

Funder

European Regional Development Fund

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D2OB00238H

Reference26 articles.

1. Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

2. Meroterpene-Like α-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from β-Caryophyllene

3. Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B

4. Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

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