Related Experiment Video
Updated: Sep 8, 2025
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Synthesis of a PPAP, Nemorosonol, Using a Tandem Michael Addition-Intramolecular Aldol Reaction
Keisuke Mitsugi1, Toru Takabayashi1, Takayuki Ohyoshi1
1Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
A strategy for constructing a tricyclo[4.3.1.03,7]decane skeleton, which is common to many polycyclic polyprenylated acylphloroglucinols, has been established. The key step was a tandem Michael addition-intramolecular aldol reaction with 3-ethoxy-1-phenyl-2-proyn-1-one, which affords a tricyclo[4.3.1.03,7]decane skeleton having a benzoyl group at the C8 position and an appropriate oxygen functional group at the C9 position. This synthetic strategy led to the total synthesis of nemorosonol, which was accomplished in 12 steps from 2-methyl-2-cyclopenten-1-one.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
09:34Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
C–C Bond Formation: Aldol Condensation Overview
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Intramolecular Aldol Reaction