A Convergent and Stereocontrolled Cycloaddition Strategy toward Eudesmane Sesquiterpenoid: Total Synthesis of (±)-6β,14-Epoxyeudesm-4(15)-en-1β-ol

We present in this report the development of a convergent and highly stereocontrolled cycloaddition strategy toward the synthesis of C-1, C-6, and C-14 tris-oxygenated eudesmane sesquiterpenoids. This approach was demonstrated in the first total synthesis of (±)-6β,14-epoxyeudesm-4(15)-en-1β-ol (1),...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2012-05, Vol.77 (9), p.4217-4225
Main Authors: Wang, Cui-Cui, Li, Wei-Dong Z
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Sesquiterpenes, Eudesmane - chemical synthesis
Sesquiterpenes, Eudesmane - chemistry
Stereoisomerism
Terpenoids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We present in this report the development of a convergent and highly stereocontrolled cycloaddition strategy toward the synthesis of C-1, C-6, and C-14 tris-oxygenated eudesmane sesquiterpenoids. This approach was demonstrated in the first total synthesis of (±)-6β,14-epoxyeudesm-4(15)-en-1β-ol (1), a structurally unique ethereal eudesmane sesquiterpenoid, via an effective Diels–Alder construction of a compact functionalized tricycle intermediate from readily available N-benzylfurfurylamine (2) and homoprenyl maleic anhydride (3) as the C5 and C10 building blocks, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300556r