Total synthesis of (±)-villosin C and (±)-teuvincenone B

Herein, we report the first total synthesis of 17(15 → 16)-abeo-abietane diterpenoids (±)-villosin C (5) and (±)-teuvincenone B (4) in 11 steps. The A/B/C ring system was assembled via a modified three-step sequence on gram-scale, while the D ring was constructed by intramolecular iodoetherification...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-01, Vol.11 (2), p.472-476
Main Authors: Jin-Xin, Zhou, Ming-Jie, Yan, Xiao-Yu, Shi, Yue-Qi, Wang, Hong-Yan, Shen, Xu-Dong, Mao, Wang, Jie
Format: Article
Language:English
Subjects:
Diterpenes
Iodination
Liquid chromatography
NMR
Nuclear magnetic resonance
Organic chemistry
Oxidation
Synthesis
Valence
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, we report the first total synthesis of 17(15 → 16)-abeo-abietane diterpenoids (±)-villosin C (5) and (±)-teuvincenone B (4) in 11 steps. The A/B/C ring system was assembled via a modified three-step sequence on gram-scale, while the D ring was constructed by intramolecular iodoetherification. This synthesis relied largely on the rational design of the order for oxidation state escalation (C6/11/14 → C7 → C12 → C17), which was realized through sequential benzylic iodination/Kornblum oxidation, Siegel–Tomkinson C–H oxidation and iodoetherification. In addition, villosin C (5) and its epimer (5a) were found to have indistinguishable NMR data and the correct configuration for villosin C was elucidated by comparing HPLC trace with a natural sample.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01841e