Construction of the tricyclic core of steenkrotin-type diterpenoids via intramolecular [3 + 2] cycloaddition

Jun Xuan; Saiyong Pan; Yuanbao Zhang; Bin Ye; Hanfeng Ding

doi:10.1039/c4ob02439g

Construction of the tricyclic core of steenkrotin-type diterpenoids via intramolecular [3 + 2] cycloaddition

Org Biomol Chem. 2015 Feb 14;13(6):1643-6. doi: 10.1039/c4ob02439g.

Authors

Jun Xuan¹, Saiyong Pan, Yuanbao Zhang, Bin Ye, Hanfeng Ding

Affiliation

¹ Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028, China. hfding@zju.edu.cn.

PMID: 25535835
DOI: 10.1039/c4ob02439g

Abstract

A concise and diastereoselective route to the angularly fused [5-6-7] tricyclic carbon framework of the steenkrotin-type diterpenoids was reported. The key features of the strategy are based on an intramolecular nitrile oxide/alkene [3 + 2] cycloaddition and a regio-selective aldol/dehydration sequence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism

Substances

Diterpenes